Since mid 2025 Zac Posen has been the VP and Creative Director for Gap and Old Navy which has elevated these brands into a new realm of stylish, but affordable fashion. The colors are richer and more intentional. The silhouettes and styles are on trend. And their shoes and accessories have especially leveled up. They should not be overlooked while you’re building out your spring wardrobe!

Now let’s tackle the inevitable question…

Does a change in price mean a change in fabric, quality, fit, sustainability and production practices, etc? In some cases, sure. It all depends on what you prioritize. You can find a ton of 100% cotton pieces from Gap brands. They also have CashSoft (Gap) and SoSoft (Old Navy) that replicate the feel of cashmere. Is this the same as 100% cashmere? No, but it’s also not $170 for a sweater.

I’m a big believer in high/low dressing! I’ve talked about this at length in another post which I will link at the bottom of this post, but for now let’s get to the good stuff.

I’m breaking down my favorite pieces below that I think you should buy. And the best news is, Gap is currently having a Friends & Family 40% off sale* so you can really shop without abandon… and is there anything more fun than that? I think not.

As a note, all links below are affiliate links <3 You can also shop everything from this collection here.

The Super Dupes.

Listen, dupes, are not always good thing. When a small business’ unique designs go viral and are immediately ripped off and mass produced by companies like Shein, we should not support them! I watched this happen to a knitwear designer, Hope Macauley, and it was devastado. Her signature chunky sweater was fully knocked off (down to the exact hues and color placement) by Shein and sold for a fraction of the price. Brutal.

But… when an already mainstream store like Aritzia releases a pink striped short sleeve cashmere polo and another (more) mainstream store like Old Navy releases a similar one during the same season, it’s a different story. Neither one invented the pink striped short sleeve polo. They’re massive corporations, not small designers.

So with that in mind, here are the super dupes I’ve found at Gap and Old Navy and where I saw their more pricey counterparts:

• Cream and pink polos: Old Navy $27.99 | Aritzia $128

• Black wedge thong sandals: Gap $69.95 | Reformation $298

• Studded jeans: Old Navy $29.99 | Reformation $218

• Tailored black blazer: Old Navy $35 | Aritzia $228

• Jean mini dress: Gap $79.95 | Reformation $198

• Gingham blouse: Gap $69.95 | Reformation $168

• Blue boyfriend overshirt: Old Navy $23.99 | Aritzia $88

• Black and gold belt: Gap $49.95 | Aritzia $78

• Yellow cardigan: Gap $69.95 | Reformation $198

PS — At the time of publishing (3/13), Gap is currently having a 40% off sale, so take 40% off all prices listed above and smile bc of how much you saved!!!

I also included the current price at Old Navy which subject to change depending on when you read this.

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Shoes + Accessories.

God these shoes are good. Ballet flats, thong sandals, and wedge heels will be hot this season. I’d rather have a few cost effective options than one splurge for the season. But you do YOU. Gap also has high quality jewelry! Ana Luisa is Gorjana adjacent, but with Gap’s sales you can get them discounted all the time. And the ruffle socks are my favorite consistent Old Navy buy.

Thong wedge sandals | 3-pack ruffle socks | Crochet bag with bamboo handle (ok Gucci vibes) | Burgundy east-west shoulder bag | Cream v-shape ballerinas (size down!) | Studded platform wedge sandals | Gingham tote | Leopard belt |Tan espadrilles | Ana luisa earrings | Black and gold belt | Black and silver belt | Wedge strappy sandals | Hot pink tote

Outfit inspo.

I wanted to show how easy it is to recreate outfits that you see on Pinterest/social media and style them using more affordable pieces. Make no mistake, I love a fancy outfit from a fancy brand! But I also think being crafty with mixing high-end and affordable items is a great muscle to strengthen.

I did a deep dive on these looks on my TikTok, but to recap:

• Gap has always done denim well, it’s a core product of their brand. So you can always trust that these pieces will be well tailored and hold up quality-wise.

• Old Navy sizing tends to run big, I almost always size down. For mini dresses I also get petite (I’m almost 5’6) to ensure they’re actually mini.

• Mixing prints is a fun, easy way to make your outfit look cooler and more intentional. Adding the leopard slingbacks to the polka dot mini dress gives it some edge.

• When wearing baggy bottoms, I like to wear a tight top. This will give the outfit structure and balance. Some girls can do baggy on baggy and look chic, but I just feel like I am wearing pajamas.

• Athleisure is my favorite thing to elevate! The trick is to pair it with things that are not so sporty. Instead of wearing a scuba zip up with a tennis skirt, opt for a cashmere cardigan and toss it over your shoulders. Bring a real purse instead of a one of those Lululemon fanny packs. I also think this is the spring/summer of ballet flats with workout clothes…… and I’m not mad about it!

• OH — AND YOU CAN SHOP ALL THE GAP BRANDS TOGETHER AND CHECK OUT AT THE SAME TIME. Sorry for yelling but that is really good news.

You can find the items above here.

I hope I’ve convinced you to do some spring shopping at the Gap brands! My dream is for you to immediately shop the sale and be absolutely delighted at how many cute things you got and how much you saved.

Spending money is soooooo fun. Saving money and still looking cute is sooooooo much funner.

xx, Caylee

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Last week I was hit with an evil case of strep throat which had me bedridden for a a few days. I say evil because it came on the same day as the massive blizzard that swept the city (rude) and the same week I was supposed to travel across the country for one of my best friend’s bachelorettes in our college town of Santa Barbara, California (incredibly inconsiderate!).

It’s one thing to get a little common cold. It’s another to have a diabolical fever during the depths if winter when you have 2 days to PTO pending and 80 degree weather ready to welcome your sun-starved skin. Needless to say I had a bit of an existential menty B.

New York is a city of skyrocket highs and hellish lows. And being properly sick in the city is especially punishing. No one wants to call an Uber to Urgent Care when they’re running at 102 degrees… add dirty, slushy snow in the mix and a routine bacterial infection becomes a sick curse of universal karma—what did I do to deserve THIS? I was being such a drama.

Some moments of clarity that came as the week went on:

• Antibiotics are amazing! Science and medicine are amazing! Yay for it not being the flu!

• Spring is coming. Deep, late winter is a season I did not experience until I moved to New York 5 years ago. So much will change energetically when we spring forward this weekend. Hallelujah.

• Fomo really sucks but this too shall pass. There are margarita and sun-filled weekends with these women on the horizon.

• Living alone is challenging but it’s a good reminder in how capable and strong you are… but, also:

• NYC is a small town masked as a big city and people treat it as such! One of my friends had Pura Vida smoothies and juices and treats delivered to my doorstep. Another dropped off soup (in a bag with a bow!). There’s an understanding here of how little acts of love go a long way and I’m grateful to have built a community of friends who care for me.

Anyway, I think I might have needed one of those shake you up moments and good cries. I felt better once I got it all out.

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Turning 34.

I turned 34 in Feb! At dinner, my friend asked me how I felt about 33 and I was proud to say that 33 was one of my most favorite years. The first few years of my 30s felt tumultuous and disconnected. But last year was peaceful, centered, and happy! What more could you want out of a yearly reflection?

I launched my Substack on my birthday last year and having this as a creative outlet has done wonders for my mental health. It feels like such a natural expression of energy and made me realize: if you do things that make you feel like YOU… goodness will follow!

Hoping to channel that same energy into 34 (and beyond). And if you’re new to the Extra Dressed community—first of all, hi <3—please give my very first post a read. I think it’s a great introduction to who I am and what to expect on here!

Jessica McCormack taste on an Anthro budget

A year+ ago I fell in love with this Jessica McCormack diamond choker necklace. Unfortunately for me (and likely for you) it’s out of our price range…coming in at a whopping $135K, depending on the diamond.

Luckily for me (and maybe for you) I am a great look for less kind of girl and sourced a handful of pieces that give the same vibe. Or at least an adjacent vibe. I got the Anthropologie one and wore it on my birthday and think it scratched the itch!!! Everything linked below.

1. Luv AJ | The Chrome Orb Pendant Necklace ($90)

2. Lili Claspe | Mara Oval Charm ($45)

3. Electric Picks | Old Money Necklace ($98)

4. Heaven Mayhem | Gaze Choker ($980… still a deal, lol)

5. Anthropologie | Gem Pendant Chord ($50)

6. Heaven Mayhem | Solene Choker Set ($150, love how these are buildable!)

7. Shashi | Roux Cuff Necklace ($187)

8. Anthropologie | Bezel Pendant ($48)

9. Shashi | Lasso Silk Necklace ($110)

10. Alexis Bittar Liquid Lucite Collar ($295)

11. Veronica Beard | Cord Pendant ($150)

12. Luv AJ | Marais Pendant ($99)

As a head’s up, everything linked below is an affiliate link!… and if the $135K necklace is in fact in your price range, please let me know. I will create an affiliate link JUST for you <333333

The Yes Pile — everything I loved in February

Ooooo there’s something about a birthday month that makes shopping hit even harder! I also included some of my favorite bites and sips, activities, reads, pods, etc.

• I’ve been listening to this playlist on repeat. It’s great for WFH and cooking and probably also good for makeouts but I’ve yet to test the theory. So please do, and report back!

• This Eberjey bralette is a g damn dream. It’s soft and lifting and invisible under clothes. I am so glad I popped into the store and treated myself to this. It feels comfy enough to sleep in, but actually makes the girls perk up.

• Ossa New York Case: I am soooo in love with this thing. It makes my phone feel less like a phone and more like a cutie little accessory. Consider her extra dressed.

• Old Navy and Gap are popping TF off for spring. I think it might warrant a full post because they are coming for you, Aritzia. But I really love this short sleeve polo, ballet flats, and structured blazer

• Summer Fridays Lip Balm: I think that this might be my favorite lip balm of all time? I recently got Brown Sugar and it’s pretty — but the best one is Pink Sugar. I love the scent and the sheerness. If I could have these on auto-subscribe, I would.

• Experiment Beauty is going to be huge this year. Some products just have IT and these ones really do. The Super Saturated Serum is perfectly viscous and juicy, which leaves your skin hydrated and plump. But the Molecular Mesh feels like silk against the skin. Not quite a gel, not quite a cream, somewhere in the middle. 10/10 recommend.

• Loving this podcast Articles of Interest - all about the ins and outs of the fashion industry. The Made in the USA episode way EYE-OPENING. If you are intentional about your shopping or curious how things are made, I highly rec. My kind of investigative journalism.

• Circus by Sam Edelman Zoey Cap Toe Flats. Like HELLO? I’ve never felt so soon by an Instagram ad.

• The cutest bag for spring is one that has tulip handles. Edie Parker is a branding queen and this bag is so thoughtfully created… she deserves her flowers ;)

• Nivea Cocoa Butter Lotion. Hydrating, fast-absorbing, smells like a damn dream, leaves skin silky for hours and costs < $10? Mmm yercominghomewithme.

• For NYC Locals, my favorite bites were:

  • Breakfast burrito from High Life Burger, just trust me and my California roots

  • The mixed green salad and pomodoro pizza from Gjelina

  • Spicy cucumber mag from Rintintin, one of my favorite margaritas in the city and maybe the world

  • If you like creamy, sweet drinks than the Dolce Vita latte from Fellini will be your bestie

  • The cinnamon rolls from Noa (WV) and Hani’s Bakery (EV) were incredible, but nothing will ever beat the cinny b from Losers!!! Order ahead and pickup on Sundays.

xx Caylee

Thank you for reading! If you enjoyed this post you may also love The Dressing Room, Volume 1

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Everyone on the internet is always talking about habits that help you level up, optimize, and maxx your life but this post is NOT like other boys. I’ve already written about ~the whimsical habits~ but I wanted to share some practical ones, too.

I’m not going to preach about having a morning routines (bc I myself can’t seem to stick to one) or getting 10K steps a day (even though you WILL be happier and more fit if you do), but I am going to share the niche things that make my life… better.

These are little things that make made my day-to-day life run more smoothly. Mentally, physically, emotionally… they help me manage all the -lys.

And it’s worth noting that aside from a couple examples, these are not products that I am suggesting you go out and buy. But rather, simple but significant* habits for normal people.

*RIP Don Draper, you probably would have loathed (but secretly loved) Substack.

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13 little habits that might make your life better:

1. Use the block button with as much frequency and conviction as you hit follow. I have hundreds of people and accounts blocked across my social media platforms. I personally see only positives from this! The internet is insane—how wonderful that you can protect yourself from people and accounts that make you feel anxious, bad, angry, envious, etc. with the click of a button. Unfollowing and muting works, too, I guess, but where’s the fun in that?

2. Have an airport routine. Keep the pouch of all your plane needs — hand sanitizer, lip balm, headphones, eye mask, aspirin, etc — stocked so you don’t have to think about it. Keep loyalty points with one or two airlines. Schedule your Uber ahead of time or block your schedule to take public transit. Wear the same airport outfit and opt for something a little more put together than yoga pants. I’ve replaced my leggings with equally comfy and infinitely more chic track pants and instead of a sweatshirt I opt for a cashmere cardigan.

3. Always have ramen in your cupboard. Interchangeable for whatever your easy, zero ingredient meal is. I travel a lot (as seen by my airport routine) and always get back to my apartment late and hungry. Having a no effort, satisfying enough meal at the ready is always a ‘pat myself on the back’ kind of relief.

4. Rent clothes for special occasions. I love the novelty of a new outfit. I do not love the toll that takes on my bank account. Renting gives you the best of both worlds. I’ve tried them all and Rent the Runway is best for high-quality items like dresses and coats. Fashion Pass is best for trendy, one-off pieces. Pickle is great if it’s popular in your city. Nuuly is the most hit or miss and undoubtedly the most time consuming, but they have great brands.

5. Buy your books from your local bookstore. You don’t have to shop small for everything, but try to consistently shop small for *one* thing. Books are art and local bookstores are their galleries. I like to keep the cash flowing in that immediate community ecosystem. This is a fun way to ritualize a hobby and break free of mindless Amazon clicks.

6. Set-up a monthly/quarterly/yearly donation to a cause you care about and put on auto-pay. A year ago I joined the NY Young Lions which is a group that benefits the NY Public Library system. I make a monthly payment and get to attend fun events and know I am contributing to something important in my city. I also make a small donation to Planned Parenthood each month. Both are tax deductible and I don’t even think about them. Set them, forget them, make an impact.

7. Solve your #1 beauty pet peeve and never skip the upkeep. There are two things I know to be absolutely true: I feel one million percent better when my nails are done and I don’t have the energy for a manicure every 2 weeks. Solution: a Russian manicure every 4 to 5. They are more expensive than a standard manicure, but they NEVER chip and look pretty much perfect until your next appointment. Plus my nails are strong underneath and you don’t have to soak your fingers in toxic acetone to get them off. I have a standing appointment and it’s baked into my ‘sunk cost’ budget.

8. Have a basic understanding of what’s going on in the world. This is especially true in your 30s and beyond. At the very least, having a general knowledge of what’s happening around you makes you a more attractive and interesting conversationalist. At most, you can change the world!!! You don’t have to be plugged in 24/7 to stay up-to-date. Limit your news to a 15-minute podcast or a daily email newsletter. Follow one specific journalist that you respect. But being an active participant in the happenings of your city/state/country is just part of being a responsible adult. Apathy is out.

9. Weave audiobooks into your them into your media consumption. If you enjoy listening to podcasts, you’ll love listening to memoirs and other non-fiction on audio. What they lack in podcast host banter they make up for in rich storytelling. They also count towards your reading goals! (If you disagree please argue with a wall <3) If you have Spotify premium, hundreds of these are included with your membership and I have tons of recommendations. Maybe I’ll write a separate post, but in the meantime: Strangers by Belle Burden (hot right now), The Uncool by Cameron Crowe, and How to Murder Your Life by Cat Marnell.

10. Figure out what calms your nervous system. We all have things connect us back to our center. It’s personal and might require a week of paying close attention to where you feel most at peace. For me, it’s writing in my journal, reading before bed, and doing little crafts when I need a screen time break. For you it might be going for an afternoon walk, meditating, or taking a bubble bath. Pencil in non-negotiable time for whatever tickles your fancy.

    

11. Tailor your clothes. Looking chic is less about what you are wearing and more about how it falls on your body. Spend the $20-$50 extra dollars and have something that fits your body perfectly. You’ll be surprised at how much more often you find yourself reaching for that jacket/pair of pants/dress/etc.

12. and in a similar vain… Get things fixed! We are part of the generation that throws things away instead of fixing them. The strap broke on my favorite pair of heels and they were only $50 from Zara so I was quick to rationalize a new pair. I was devastated when I went online and they were sold out! I ended up taking them to the cobbler (how cute is that, btw, a cobbler) and got them fixed up for $10! Huge lesson for me. You can also replace the soles of your shoes to extend their life and comfort levels. City living learnings!

13. Turn on a 10-minute end of night timer and tidy up until it rings. This has made me so much more organized! I am a night owl, often working into the late evening, so by the end of the day my house feels especially lived in. Instead of letting it overwhelm me, I set a 10-min timer and tidy up what I can. Pretty much everything gets done in that time frame and it makes the task of ‘closing up the house’ at 10pm more manageable.

YOUR TURN. Please share the little things you do that make your life easier and better and richer and more fun!!!

xx Caylee

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Thank you for reading! If you enjoyed this piece you may also love 33 Lessons in Girlhood.

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Regardless if my conversation heart says [x] taken or [x] single or [x] it’s complicated, I will always welcome Valentine’s Day with open arms because she’s fun and fabulous and, let’s be real, for the girls. So if you’re sad about being single for the occasion I am kindly suggesting a reframe for two reasons:

1. Pouting about it won’t change anything so you mind as well do a Sheryl Sandberg and lean TF in. A day of frivolity and whimsy awaits!

2. VALENTINES DAY IS ON A SATURDAY. Imagine wasting a Saturday in bed, doomscrolling and eye-rolling when you could be live laugh loving all over the place & celebrating all the love you DO have in your life. Love from yourself, your friends, your fam, your pet, your celebrity parasocial relationship, your bodega guy, your fictional book character boyfriend… Love actually is all around.

To get you ready, I’ve concocted a dreamy recipe of plans and purchases for you to make the most of this capitalist love affair. And if you do find yourself coupled up this year, everything will still apply! Just add your S/O to the plans OR dump them, whatever feels like it will bring you the most peace :) :) :)

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5 ways to make the most out of your Valentines Day:

Write a love letter. Either to yourself, a friend, or the future lover you’re conjuring up. Valentines Day is all about romance and there’s nothing more romantic than honey-dipped words of affirmation! Keep it in your journal or if it’s addressed to a friend, send it via snail mail with a special stamp. To get you thinking…

Valentine’s Day Journal Prompts:

• What are three things I genuinely love about myself and why?

• Describe your perfect Valentine’s Day in extreme detail - who are you with, what do you do, how do you feel?

• What scents, colors, textures, flavors make me feel most like me?

• What are some of the qualities I admire in people that I love?

• Pick a song, movie, or book that gives you all the fuzzy feelings and explain why it feels special to you.

Take a level 10 everything shower (et al) the night before. You should be dolphin smooth and two shades darker with light discoloration on your wrists. You will have used all the devices you swore you were going to use every night in 2026!!!! (good time to revisit those self-care goals). By bedtime you should feel both disgusted by the amount of propaganda you have fallen for and purchased and delighted with how you’ve successfully marked yourself safe from the winter scaries.

Buy at least one traditional Valentines treat. Bottle of champs. Bouquet of flowers. A box of chocolates or other sweet indulgence. A snuggly teddy bear. Lingerie! Whatever tickles your fancy. Feeling ‘without’ is a crummy feeling (as a single girl I can relate, so trust that this is very sincere!). But I think what makes that feeling bubble up to the surface on Valentine’s Day is actually being without the STUFF. So don’t let yourself come home to a flower/chocolate/teddy-free house.

Make plans on actual Valentine’s Day. With a friend or with yourself! The rule is that your plans must be plans that require actual planning. We’re not playing anything by ear on a holiday weekend. I’ll be with my bestie at the ballet and afterwards we are enjoying an early dinner at a swanky french restaurant. Drinks will be drunk. Purchases will be made.

Some ideas…

• See “Wuthering Heights” and take a weed gummy before or sneak in a bottle of screw top rosé.

• Visit a museum that’s been on your list forever but you’ve never gotten around to it. Choose the guided audio tour. Eat at the café.

• Treat yourself to a unique self-care experience like a head spa or bath house. Tons of these on Groupon.

• Have a craft day. I am currently obsessed with bedazzling and love this hair clip idea!

• Workout class b2b matcha/iced coffee b2b light shopping and lunch. Name a better day.

Dress like you’re going to spend the day with the love of your life. For starters, you should be one of the great loves of your life. And I don’t mean that in a self-indulgent way, quite the contrary. You spend 100% of your time with yourself so you mind as well start loving the shit out of her. Second, if you believe in the power of manifestation, then you know that embodying your future is kinda the whole whole thing! Get ready intentionally. Wear something that feels like the best version of you. I would suggest wearing pink or red but I know that my threshold for kitsch is higher than most so I give you space to wear whatever makes you happy.

And there you have it, a Valentines itinerary so sweet you might actually romanticize being unattached at this moment in time!

xx Caylee

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Thank you for reading! If you enjoyed this piece you may also love Poor little single girl :( and 33 Lessons in Girlhood.

Getting the perfect gift for a guy feels a lot like this ↓ meme, absolutely delighted and tickled with pride. It’s easy to buy things you know your girlfriends will love, but when your significant other feels seen in the gift you got them… sweetness like no other!

Since I am currently unattached I decided to shop for My Perfect Guy™ and your S/Os instead!!! I feel like splurge gifts are reserved for birthdays and Christmas, so everything is quite cost effective, too.

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14 gift ideas for your Valentine:

(11 gifts, 2 sweet gestures, and 1 spicy add-on if he’s been an especially good boy)

1. Corridor ball caps [LA + NYC]. Everything Corridor does is cool, but their ball caps feel especially elevated with their fabric, font and color choices. I have a tote bag from here and everything is high quality and worth the cost.

2. Signet ring. A ring for Valentines Day, omg! There’s something so effortlessly hot about a signet ring. Engraved or not, I like how much surface area it takes up and the brushed silver is my personal favorite.

3. Framed photo strips. The cutest, easiest DIY! All you need is a piece of fabric or colored paper and a an old frame. You can find tons of frames second hand shops like Goodwill. Hot glue the fabric on the back of the frame’s insert and glue your photo strip on top! Easy peasy. If you’re totally anti-craft or want it to look even more sophisticated, any frame store can help make this happen.

4. Owala water bottle. There is no better water bottle on the market! You can fountain drink or sip from the straw (preferred) and there’s a hook that makes it easy to carry it into the gym with phone/keys/wallet trifecta also in tow. Tons of cutie manly colors to choose from. Time to upgrade his free tech co’s merch to something more useful!

5. Sweet jackets [one + two]. I am obsessed with this brand. It helps that the founder is really cute and posts all the drops on TikTok. His Grandfather is the older gentleman in all the pictures which is, indeed, so sweet. Very west coast coded and high quality, unique pieces.

6. Nodpod weighted eye mask. I left my NodPod at my best friend’s house and she let me know that her husband had tried it out and had the best sleep ever. I’m an insomniac who has developed very particular sleeping habits, and this is one of my favorite finds. The weight is light, but adds an extra layer of comfort. One of the gifts you don’t really want to buy yourself but once you have it, you can’t live without it.

7. Vintage magazine of his favorite band. A friend once gave me a 1978 People Magazine with Dolly Parton on the cover and remains one of the most thoughtful and unique gifts I’ve received! Find one of his favorite band on eBay and give it to him for a coffee table addition—or frame it so it can be hung in his room.

8. Necessaire body wash & lotion. Every man not-so-secretly loves taking a shower at his girl’s house because of all her delicious soaps and lotions and potions. So give him his own luxe shower moment with a super sudsy, sleek body wash from Necessaire and a matching body lotion. Plus, they look good in every bathroom.

9. Custom engraved lighter case. Hot hot hot. You can engrave his initials, a cute pet name or something mushy and Valentines coded. Regardless of what it says, a very trés sexy thing to have.

10. A fiction he will enjoy. All guys typically prefer reading non-fiction (sweeping generalization, sorry), but they probably just haven’t found the right fiction novel! I’ve given a couple men in my life (an ex and my Grandpa, specifically) a copy of Beneath a Scarlet Sky by Mark T. Sullivan is was very well-received by both! A girlfriend of mine gave her Dad a copy for Christmas and the sentiment was the same. It’s a fast-paced adventure set in Italy during WW2 that’s based on a true story. One of the most gripping stories I’ve ever read. Race cars, ski resorts, war, love, friendship, family… all the makings of a five-star read.

11. Ranger Station candle in Santalum. God this scent is divine. It’s what the inside every swanky whiskey bar in a ski town should smell like. Elevated, musky, androgynous, and not too potent. When the candle runs out you can repurpose the glass for cocktails! Pair it with his fave liquor?

12. Make him a Spotify playlist and change the image to one of you guys and name it something extra* special <3. This is an easy one but the updated cover makes a big difference!

13. Lingerie but only if he’s received outstanding marks in the BF department as of late! I personally would like to wear/give the lingerie rather than receive it. I lean cute not sexy (can’t help myself!) but I think For Love and Lemons has the best selection of tasteful, gorgeous little things.

14. And of course, seal it all up with a mushy, gushy, spicy love letter. Something he’ll want to keep in his bedside table to read when he wants to feel your cheekiest energy.

Happiest Valentines, lovebirds! I’ve linked my entire Valentine’s Day Edit here if you’re also shopping for yourself or your bestie <3

xx, Caylee

Thank you for reading! If you enjoyed this post you may also love Always on brand! Easy ways to find and refine your personal style.

I had this whole article written and ready to publish last week and it felt so tone deaf given the events in Minneapolis I decided to scratch the whole thing and start anew. I trust that we can talk about laser hair removal another time!

My feelings over the course of the last week have oscillated from devastation and rage to gratitude and optimism and riding the wave of all of them is emotionally taxing. I’m sure many of you feel the same. Quite simply, it’s a lot.

While my intention for Extra Dressed is to create an online world that’s as indulgent, playful and fun as its name suggests, it would be dishonest of me to ignore some of the other things I am feeling.

So the goal of this week’s Dressing Room is to acknowledge how overwhelming everything feels and rather than sit in that negative energy, offer some ways that we can seek joy and keep our whimsy alive!!!

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Action is the antidote & the kids are alright.

I wrote an article over the summer after attending the No Kings Protest that focused on action as the antidote. It remains true! It will always be true! Helplessness is a feeling that we cannot indulge because there’s always going to be a way for you to make a positive difference.

If you’re looking for ways that you can get involved in and/or give back to your community, I encourage you to give it a read ↓

Another resource that my Mom shared with me this week is an app called 5 Calls: Contact Your Congress. It’s a fabulous app and an easy way for you make a political impact. After entering your zip code, the app lets you know which legislators are in your area and provides you with their phone number and a script to read.

PSA: Calling your representative is the most effective way you can influence policy!

Replace your doomscrolling with 5 minutes of phone calls. I promise you will feel better, if only slightly.

I was also deeply inspired by the videos I saw online covering the hundreds of thousands of students who walked out of their classrooms on Friday to protest ICE. These walkouts happened in all corners of the county — from Texas to California to Georgia to Washington to Utah — and seeing all these young people with signs in support of their neighbors filled me with a lot of hope! If you want to get your algorithm onto #HopeTok I suggest you take a peek.

Whimsy in practice = bedazzling Aquaphor

My most viral articles on this app have been about whimsical habits to keep you from spiraling into the darkness. I love that of all my writing, these have garnered the biggest reach! Without parroting the originals too much, whimsy, to me, is intentionally making the everyday more fun and cute. And this looks different for everyone.

Maybe it’s always wearing fuzzy socks at home. Or taking the scenic route home from work every day, even if it takes 10 extra minutes. Or sending your friends snail mail for their birthday and decorating the card.

For me, right now, it’s ~*bedazzling*~.

You know that partin Legally Blonde where Elle says that endorphins make people happy and happy people don’t kill their husbands, they just don’t? That same logic applies to bedazzling. It’s statistically impossible to be sad when you’re gluing rhinestones onto inanimate objects*.

I’ve found that the more random the object, the more whimsy is conjured up in the moment and the longer it lasts. How silly to glue rhinestones on a tube of Aquaphor! How fun to see it glisten and sparkle on your bedside table day after day, night after night!

This level of harmless frivolity adds tangible amounts of joy to my life. If you’re looking for a low-barrier-to-entry craft that will distract your mind, keep you off your phone, and leave you with a sparkly little something… I highly suggest.

*source: me.

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The Yes Pile — everything I’m loving lately and think you will, too.

I had a lot of loves this month:

• The Uncool by Cameron Crowe is one of the best memoirs I have ever read/listened to! A natural storyteller with a pretty incredible life story to share. You likely already know about his teenage stint as a Rolling Stone reporter for a touring band as it was later adapted it into a screenplay (yes, speaking about Almost Famous). But that’s only scratching the surface. He has hundreds of encounters and experiences with some of the most famous people in the world from David Bowie to The Eagles, but he recounts them with humility and kindness. Could not recommend more!

• Saie Dew Bronze Soft Focus Sculpting Liquid Bronzer is sooooo good. I saw a gal on TikTok use it and it blended so effortlessly I was sold on my second watch. It adds warmth and dimension without feeling like you’re wearing a full face of makeup. I also use it as an eyeshadow! My favorite makeup find from the last year.

• Everything that from writes is internet gold. I love his mind! I love his words! And giving a SWM (straight white male) an unrequited compliment online is not something I am doing frequently. He deserves it, ok! A lot of his posts are paywalled now (get that bag, babe). But he removed the setting on a couple so poor people everyone could enjoy them:

  Uncynical

  45 things that are true

  I am not very old. I am not very wise. But there are a few things I know to be true. I think they can serve as shortcuts and solves in many situations…

  Read more

  3 months ago · 418 likes · 12 comments · Dylan

• The prebiotic sodas from Trader Joes are just as good as Poppi. I’m not going to say they’re better because I don’t have enough to go off of, but as someone who drinks a sparkly beverage at least once a day I give them a heavy stamp of approval.

• Scallion rotisserie chicken in a bag. The perfect meal to cook for one. I’m so happy when my FYP gives me something that actually changes my life!

• Yoga Space, Greenwich Village is my favorite workout studio in downtown Manhattan. I was introduced to it this summer by a friend who frequents their Greenpoint location, but I go to GV since it’s in my neighborhood. The studio itself it gorgeous, the teachers are cool, and there’s a great range of workouts: traditional yoga, mat pilates, sculpt, and stretching, to name a few.

xx Caylee

Thank you for reading! If you enjoyed this post you may also love:

During the early days of the pandemic I was spending time with my parents in Park City, a beautiful little mountain town where they had been living for a few years. Every morning I’d wake up, layer up, and go for a long walk through what felt like a desolate and abandoned western TV set. Equal parts eerie and peaceful. Just thinking about it now brings back such a strange stir of emotions.

One day I started to listening to Dolly Parton’s America, a 9 episode podcast journey into the Dollyverse by WNYC Studios, hosted by Jad Abunrad. I was hooked from the very first episode and my morning walk x listening ritual would become a bright moment during an otherwise ominous time.

Rather than a documentary style podcast on her career and achievements, the podcast was produced in a way that explored the “why” and the “how” behind Dolly’s success. As a pop culture fixture, Dolly does something that almost all of her peers can’t seem to do. She transcends genre, class, region, gender politics, and decades. Everyone from Appalachian grandmothers to coastal intellectuals to drag queens to Republicans and Democrats all claim her as one of their own. And in April 2020, the country (& the world for that matter) was more divided than ever.

I’d always loved her music and her persona. What’s not to love about twangy country pop from a sharp, clever bombshell of a woman who’s always covered in rhinestones and butterflies? But this podcast swiftly turned my passive interest into awe. In the years since I feel like I’ve become a devoted fan, of course, but also a student who pays attention to the way she lives her life, the choices she makes, and the energy she puts out into the world.

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Here are some of the little Dollyisms I’ve picked up along the way:

1. Don’t forget your roots. Dolly’s always celebrated and respected her humble upbringing in Tennessee, it’s at the heart of everything she does. Her continued loyalty to Appalachia keeps her grounded and real.

2. Femininity is a superpower. What makes Dolly especially appealing to me, and many others, is her fearless celebration of womanhood. The glitz, the glam, the boobs, the blonde, the hyper-femme… it’s who she is! Leaning in became part of her business strategy. And she was all the more powerful for it.

3. Motherhood isn’t the only marker of a successful life as a woman. For as traditional of an upbringing as this southern girl had, Dolly’s very intentional choice to not have children was modern. I appreciate how candidly she speaks on this and how her role in her family as a sister, aunt, godmother, etc. remains one of importance.

4. Actions speak louder, and more authentically, than words. One of the most interesting parts of the podcast is the conflict and trepidation Dolly has with the label ‘feminist.’ She tends to stay out of politically charged conversations straight on and the word felt too strong, too polarizing for her… despite embodying its core values of financial independence, creative control, and self-determination. By letting her life speak instead, she remained accessible to women who might never claim the word ‘feminist,’ while still modeling its ideals. This was a veryyy nuanced and important episode for me in the podcast [Dollitics, Dolly Parton’s America].

5. Joy is radical! Dolly is fun and silly and cheeky! She lives her life colorfully and consistently chooses joy, happiness, optimism and whimsy… even when the world’s on fire.

6. Know your worth and refuse to sell yourself for less, even if the buyer is Elvis Presley. Dolly famously denied Elvis recording I Will Always Love You as his management was demanding half the publishing rights. She knew it was going to be one of her most important copyrights so she didn’t move forward with the partnership. Her intuition was right, of course, and when Whitney Houston sang it years later it become her highest grossing song of all time. Girlbo$$.

7. Generosity builds legacy. She’d be a billionaire if she didn’t give so much away! Her Imagination Library has given over 300M books to children, she donated $1M to Moderna to help fund the COVID vaccine (political actions speaking louder than words). She’s always doing good.

8. You’re never too old to try something new. Today is Dolly’s 80th birthday and she’s gearing up for a Las Vegas residency in September (which by the grace of all things good I will be attending!!!). Age is but a number!

9. Sparkles make everything better. :) :)

My favorite song of Dolly’s is Light of a Clear Blue Morning. She released a new version last Friday with Miley, Lainey, Reba, and Queen Latifah, and it’s gorgeous… but I still prefer the original.

I listen to it whenever I need a reminder that everything’s gonna be alright, it’s gonna be okay. Maybe you’ll enjoy it, too.

Happy birthday, icon. I’m so glad we exist in the same lifetime! 🦋

xx Caylee

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Naturally, I looked at my own photos from that year and was overwhelmed with the same sense of feel good nostalgia that everyone else is experiencing.

As a romantic, daydreamy type person, I always look at the past in a very rosy hue. But 2016 seems to be deserving of such colored glasses! It’s clear she really was that girl… but why? What made it so?

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In 2016 I was 24 and working at my first big-girl job (a 9-to-5). I was a social media coordinator at a boutique agency making $38K a year (lol) but it felt glamorous to me. I got to work with up-and-coming beauty brands and influencers alike, writing captions and blog posts, taking flat lay photos, and getting a peek at the wildly lucrative creator industry.

Working in social at the time placed me even deeper into the zeitgeist of 2016. Here’s a glimpse of what was going on:

• Instagram was still highly curated and limited to a single photo per post. Stories came out in August that year. Carousels came out the following. Short-form video didn’t debut on the platform until 2020.

• Snapchat released the puppy filter and the “pretty” filter and we went feral for both.

• Glossier reigned supreme. An industry disrupter that changed the way we market and shop for beauty products (…all products, for that matter). Did I want Glossier Moisturizer Rich because my southern California skin needed a heavy cream to lock in hydration during the cold 65-degree winter? No, I wanted it because it was f*cking cool and Emily Weiss was the #girlboss who said it was.

• The OG super influencers were starting to be taken as seriously as celebrities. Think Shea Marie, Amber Fillerup, Aimee Song, Marianna Hewitt, Chriselle Lim, to name a few.

• Millennial pink was everywhere. Same with colorful walls and hand painted angel wings. Puns as captions. Shelfies. Product flatlays. But first, coffee.

• Sugar Bear Hair and Flat Tummy Tea were hot. So was FabFitFun (where I went on to work the following year). We loved subscriptions!

• Ben was The Bachelor and basically every girl that was on his season became an Instagram influencer: Lauren B, Jojo, Becca Tilley, Amanda Stanton, the Twins, etc. This was the first time this happened… the reality TV to influencer pipeline begins.

• While brands were starting to get big on social, Instagram and Snapchat were still platforms you used to humble brag update your friends about your life. Connection was first, consumption was second.

Looking at this snapshot, it seems like the reason 2016 felt special is because we were straddling two timelines. We were still using social media as it was originally intended: to connect, to play, to chat, to update, to seek inspiration. But we were about to step into social media 2.0; the relentless, congested, divisive, omnipresent digital world that we live in now.

Consumption moved at a slower pace, too. I loved Tinx’s take and examples on this (you can watch her video here). But TLDR, the trend cycle was longer because we didn’t see everything, everywhere, all at once!

Your Favorite Influencer™ had a single still photo to sell you something. Or maybe an aesthetic series of three still photos. Now that same influencer is selling you something 5x a day on 5 different platforms.

When I asked ChatGPT (we’re cooked) how to become a successful influencer in 2026, this is what it suggested:

Essentially, never stop filming and posting and commenting and tagging and linking and you’ve got a chance!

Our sense of urgency is heightened because we’re inundated with an endless stream of content. We live, part-time, in a highly personalized, always adapting algorithm that feeds us everything we need and pushes us to buy it NOW! HURRY!!!! If you don’t get it right this f*cking second you might die. Or worse… you’ll get it too late and it won’t even be the Right Thing anymore.

Oh, you bought the strawberry jam cozy coquette girly pop aesthetic jacket? Haha. We’re caramel latte teddy bear mob wives now. Idiot.

In my photos from 2016, my friends and I were all wearing iterations of the same thing in every single photo we took together. Army jackets, ankle booties, chokers, criss-cross body suits, ripped skinny jeans, and no one knew how to do their eye liner.

Even the trendiest thing had a longer shelf life. Outfit repeating was normal. I remember saving up to buy a For Love and Lemons two-piece set to wear to Coachella and I wore it to death! Multiple feed posts on multiple occassions! The high I felt from having it in my closet didn’t dissipate. In fact, it’s still in my closet because it meant such a big deal.

I sympathize with the kids (and their parents) who are in middle school and high school now and trying to stay #grateful and #grounded. I can’t imagine navigating that god forsaken hormone filled time of life at the same time as TikTok Shop and Get Ready With Mes.

I wonder what we’ll be doing 10 years from now. Maybe we will just crawl into our phones and live inside the algorithm, tucked in between Japanese 7/11 ramen mukbangs and mermaid ASMR spa treatments. Cozy.

There are a bajillion other reasons why millennials especially are longing for 2016.

Most obviously, it was the last year before and ever since January 20th, 2017 we have unfortunately been living in the after. Toss a global pandemic into the middle of that and boom—2016 feels like a love dream you wish your alarm clock didn’t disrupt. It does fill me with a certain amount of glee that everyone, friends and foes, are collectively yearning for this year. At least we can agree on this one thing… even though maybe it’s not totally registering for everyone, ha.

ANYWAY.

I don’t know why I felt so compelled to talk about this in length. I’m always a bit melancholy and nostalgic over the past, but I think the social media of it all feels important to reflect on. At least for me, someone who has spent her entire career in this industry and has reaped the benefits and suffered the consequences of it at its best and worst.

If the essence of 2016 is what we want to channel in 2026, then:

• Screen time needs to be more intentional and less mindless.

• Creating needs to outweigh consuming.

• We might need to buy chokers?

• And we definitely need to be listening to more Flume.

That’s all I’ve got.

Caylee, out. ;)

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Thank you for reading! If you enjoyed this post you may also enjoy my newsletter, The Dressing Room, and 11 whimsical habits to keep you from spiraling into the darkness

Dressing rooms are one of my most cherished creative spaces. Some are better than others, but when I step into the stall with an arm full of clothes, my imagination gets goooooing. It’s not just about finding the dress, but envisioning who you’ll be when you wear it. The possibilities are endless! Dressing rooms are also the birth place of girl math (non-derogatory). A $250 item can easily become free with a quick cost-per-wear analysis and the right mindset.

All this to say, I’m taking everything I know about a beautiful brick-and-mortar dressing room experience and channeling it into this digital one.

You can expect more thoughts and musings, recommendations of all kinds, FASHUN (of course), and whatever else feels ~right~ upon sending. I hope it’s an always-fun read that sparks creativity and inspiration and excitement… like the feeling you get when you try something on and immediately add it to the “yes” pile.

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“Thanks, it’s vintage!” and other shopping revelations

When I was looking back at my favorite outfits of 2025 (as one does) I realized that many of them were vintage or thrifted or bought on second-hand sites like eBay and Poshmark. I also tried Pickle, a popular renting site in NYC and other big cities, which lead me to one of my favorite purchases* of the year. My closet gained some special one-of-a-kind items, all that felt very ~me~, despite having lived whole other lives before coming into mine.

And that’s the other thing. The romantic in me loves the story that comes with pre-loved pieces. I found a 1960s fur-trimmed peacoat when I was shopping in South Beach and my god, how I long to know her backstory. What’s a girl like that doing in 80 degree weather?! I did the only ethical thing: swiftly brought her back to Manhattan… where she very clearly belongs.

Along with these second-hand finds, I also noticed that I added some really lovely high-quality staples to my wardrobe. These are things I reach for almost daily, most notably cashmere sweaters, extremely well-tailored denim, and all around higher quality fabrics.

Both of these learnings made me quite happy! On one side, I spent more time sourcing items that are unique and make me feel alive when I wear them, and on the other, I stocked my wardrobe with foundational, evergreen elements that help keep the others grounded.

It felt like a very balanced shopping year.

If shopping intentionally, developing your sense of personal style, or investing in some of those foundational pieces is on your 2026 vision board—you’re in the right place! We’ll do it together <3

*Unfortunately for me, I did in fact pay to rent the dress from Pickle and then pay again to buy it, so at that point I could have just bought a new dress full-price… but WHERE is the fun in that???

The things I bought full-price and really love:

• Athleta Track Pants

• Agolde Denim

• Aritzia Cashmere Cardigan

• Dolce Vita Ballerinas

• Peche wool x cashmere blend coat

Trending now: word of the day

I’ve started a daily notes project called word of the day where I match a series of photos with a word they all embody. I was inspired by ’s good pairings series last year and wanted a similarly creative daily challenge. It’s been so fun!!!

Blending words and visuals has always been my cuppa tea and this feels like putting a pretty little micro story out into the world everyday. Plus, Pinterest is the only scroll free of doom.

What words should I do next? Please advise!

(seeing it like this, I really wish I did 6 photos instead of 5… live & learn, kids)

Side note: I heard a rumor that Open AI might be buying Pinterest? In which case we will need to throw the entirety of earth in the trash and try again. I simply shan’t go on if that happens. Leave my user-generated content happy place alone!

The Yes Pile — everything I’m loving lately and think you will, too.

One of my favorite parts of other people’s newsletters is where they share all the random things they are watching/reading/eating/shopping/hyper-fixating on… etc. And as someone who consumes a lot (lower screen time DID make it onto the vision board), I realized that I too have recommendations that are worthy of a share!!!

• Good Hang with Amy Poehler is one of the best podcasts I have ever listened to. You know it’s good when you elect to watch it on YouTube, dedicating to a whole hour of sit down time, rather than just turn it on during your commute. Not only does she have the most impressive rolodex of funny, endearing, successful people who are at her beck and call, she also is an expert conversationalist. She will make an excellent late night talk show host one day…soon. I love them all, but some of my favorite episodes are Kate McKinnon, Ina Garten and the greatest of all, Cole Escola.

• The Magnolia Parks series by Jessa Hastings has me in a forever chokehold. I am not much of a romance reader, but there’s something about Jessa’s writing that transports me back into the fuzzy, manic, magical feelings of your first love. The good, the bad, and definitely the toxic. It’s kind of like Gossip Girl with its upper echelon class of characters, but I always think of the Beckham kids when I’m reading it. Yes, as in David and Victoria Beckham’s kids. I don’t think I’ve ever re-read a book (why not, I wonder?), but I re-read the first three of this series back-to-back-to-back on a recent trip to London. Would make a great winter into Valentine’s read.

• I’ve been preaching my haircare routine to anyone who will listen, including my parents’ real estate agent and a random girl at the airport who very sweetly, but lightly complimented mine. To set the scene, you need to know two things:

  • 1) I’m an insufferable freak when it comes to hair. It’s just my thing. Well one of my things. I always think things are worse than they are and will cry if more than the agreed upon length is cut. I’m not proud of it, but I feel it’s important for you to know.

  • 2) I got a #botched cut and keratin treatment over the summer… and I know that you’re probably not taking that seriously considering what I just told you BUT the hairstylist I went to for a correction told me, and I quote, “most people are being dramatic when they say they got a bad haircut but this is terrible.” Mhm. I’ve never been simultaneously validated and horrified.

  • All that to say, the two products that healed my hair and have it in an incredibly healthy, hydrated state are the Olaplex Serum #9 and the L’oreal Glossing Treatment - shine on you crazy diamond! I also use the NatureLab. Tokyo Scalp Scrub once a week and have been preaching this for years.

  • You can see it post everything shower and blowout HERE.

• My latest food obsession is the kimchi from Trader Joes. Does anyone else eat this thing by the tub? My gut health is about to be insane. It’s so flavorful, I put it on everything.

• I think that of Style Toast is one of the cutest follows on the internet. She always makes these fun quizzes for us to do, like a little fashion tarot card pull.

  style toast

  064: who am i?

  After two and a half weeks in limbo, I’m coming back to myself…

  Read more

  3 months ago · 60 likes · 4 comments · Brooke

• I know that everyone and their mom is watching Heated Rivalry, but considering I was catching up with a veryyyy cool friend yesterday who said, “what’s that?” when I asked if she had watched it… it STILL warrants a plug. Watch this show. And watch it with your boyfriend bc you want a boyfriend who appreciates all aspects yearning and romance ;)

OK, that’s all for now. See you in the next Dressing Room.

xx Caylee

Thank you for reading! If you enjoyed this post you may also love An end of year reflection that will make you feel warm & fuzzy inside

But before you lean in, don’t forget to look back! We completed another lap around the sun and though 2025 felt capital B BLEAK at times, it was also glittered with a lot of moments worth celebrating once more.

So, here’s the end-of-year reflection ritual you should add to your agenda for that week between Christmas and New Years where everything feels slow.

PART 1: ROMANTICIZE YOUR YEAR IN REVIEW.

Create an album on your phone titled Best of 2025 (or whatever clever iteration of such verbiage you decide).

Open up your photos on your phone and type ‘January 2025’ into the search bar. Scroll through the catalogue of photos and videos and notice what stands out and sparks joy. Add those photos to your Best Of album and repeat with each month of the year.

You’ll notice that some months there will be an endless amount of amazing moments to choose from. Others will have you looking at your daily routine with softer, more inquisitive eyes. Suddenly, the beautiful pink roses you passed on your way to work in April actually were worth stopping for!

Don’t feel like only aesthetic, Insta-worthy pictures need to go in this album. I added a screenshot of a DM that a (male) friend sent me in response to a Substack article I wrote. It made me feel really good. So into the album it went.

PART 2: THANK YOU, MORE PLEASE.

A few years ago I saw a video of a girl who said her favorite game to play with the universe was Thank You, More Please.

Essentially, when something good happened to her—especially if it was unexpected or spontaneous—she would whisper to the universe “thank you! more please!” to energetically let the world know she was happy to receive that moment and would like some more.

It’s a little phrase that seems to pop into my mind when something great happens to me. And it’s become a tradition for my end of year journaling prompt.

So, grab a pen and paper or open a fresh Google doc and ask yourself:

• What are are the moments you’re thankful for?

• What are you asking for more of, please?

• What were the BIG, easy moments you celebrated this year? The photos that easily went into the album.

• Which months were the hardest, and what little joys stuck out despite that?

• What recurring themes are in your Best Of album? Friends, travel, settings, etc.

• If did you set goals or chose a word of the year, can you see them in the photos?

WHAT’S IN A YEAR?

I made my album and did my journaling and realized that on a personal level, I reallllly loved this year. For the first time in awhile I felt incredibly present and connected to myself, my friends, my family, my work, and my surroundings. The images I selected helped me see that.

Going into 2025 I didn’t make a vision board or set a bunch of goals or choose a word of the year. I didn’t deep dive into my astrological chart and most surprisingly, I didn’t journal at all; a self-care practice that I have enjoyed my entire life. I didn’t want to overcomplicate things for myself. I needed a little break from what felt like two years of non-stop chasing. I just wanted to enjoy this particular life moment and be happy. And I’m so glad I listened to that inner voice because 12 months later, that’s exactly how I feel.

Im not sure I would have realized all this had I not taken the time to properly look back at the last 12 months and recount all the beautiful life moments and blessings that defined them!

This is me encouraging you to do the same… and to remind you that being simply happy is a really gorgeous & important goal for the year ahead :)

xx Caylee

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Give me sparkle! And bows! Colored tights! Heels in 25 degree weather! Fur cuffs and collars! If there’s ever a time to lean into fun, whimsical, and extra* dressing, it’s the holidays. In this house, Martha May Whovier is our Christmas queen.

If your calendar’s booked and busy with holiday soirees and you don’t know what to wear, you’ve come to the right place. Just remember, when it comes to holiday dressing, standard rules go out the window… and new ones apply.

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THE EXTRA DRESSED RULES OF HOLIDAY DRESSING — very (un)serious!

Inspo pics make everything easier to execute. Inspo is everywhere — start to take stock in the *styling* that makes you light up. Not just the individual pieces! I recently saw a dress on Revolve that’s pretty on its own, but the way they styled it made it really special. I took a screenshot. I’m always on Pinterest saving things I want to recreate. I actually just started a new TikTok series where I recreate some of my favorite pinspo. Trust me, having a starting point makes execution easier.

Accessories are everything. Your LBD is the perfect base for the holiday party, but let it be just that. The base! Accessories take your outfit from average dinner drab to OMG where did you get that! Headbands, bows, costume jewelry, glittery eye shadow, pops of color, a red lip, a sparkly purse… accessories are the quickest, easiest, and most cost effective choice you can make this season. These are also so easy to find at places like Target, Old Navy & thrift stores.

Sparkles spark joy. If looking at a shiny, sparkly, glittery object doesn’t make you feel warm and fuzzy inside we are not the same. I think most people love glitz and glam but are so afraid of looking tacky that they avoid it at all costs. Well, not in December you don’t. I want sparkles on my sparkles. I want (fake) diamond earrings and (fake) tennis necklaces and rhinestones where they normally don’t belong. Get over the fear and get yourself some glitter.

BTW, one of my favorite 2025 discoveries was the Fazit sparkle face tattoos. Sounds absolutely bonkers, I know. But they’re actually quite tasteful and suuuuuper freaking cute. I wore them last year on NYE, to multiple concerts, and on the beach in Miami on my birthday.

Tights are fun and sexy. If you’re a seasoned Extra Dressed reader, you know that tights are one of my most consistent loves. I’m manifesting a partnership with Calzedonia because I give them so much money and free marketing. But to me, tights are to holiday dressing as sundresses are to summer… ESSENTIAL! If you are new to tights and want a classic pair, the Calzedonia Invisible Denier 20 will be your girl.

What’s even better, though, are tights that are borderline insane. Polka dots, bold colors, plaid, ones with little phrases on them. Embracing the kitsch is what levels up your look.

HOT TIP: Always size UP in tights. Whatever size you are on the back, get the next size. They will still fit snug but you will have more material to play with, preventing snags from happening.

Take an uber. Wear the high heel. Choose the coat that compliments the look rather than the drab all-black utility parka (Yuck! That’s for January!). Part of the holiday look is committing to the bit, so make lunch at home all week and treat yourself to an Uber to and from your event in the name of FASHION.

Baby pink and ice blue are holiday colors. There I said it! Maroon and it’s many variants (wine, burgundy, so scarlet it was..) are undoubtedly the star shades of the season… even down to the nails and lips. But pink is just as important! Hello, have you seen a sugar plum fairy? And there’s something so cute and cool about a frosted blue holiday color palette. OK, MARTHA MAY XMAS MORNING ROBE!

Cool girls wear whatever the fuck they want. There are going to be neutral apologists in every room you enter. Don’t dress for them. You’re going to a party! The streets and restaurants and homes and trees and bushes and windows are all decked out for the season—it would be a damn shame to not match their energy.

FULL LOOKS & SHOPPABLE LINKS:

All the outfits I want to wear this season — from Christmas parties to New Year’s Eve! Everything (+ more!!!) can be found in my ShopMy (disclaimer, affiliate links!)

link to shop with me :)

Wishing you a verryyyyy extra dressed holiday season!

xx Caylee

TY for reading! If you enjoyed this, you might also like Tights are cool (& sexy), don’t let them intimidate you and Always on brand! Easy ways to find and refine your personal style.

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Hey upper east siders. Gossip Girl here, your one and only source into the scandalous lives of Manhattan’s elite…

No piece of media has shaped me more than Gossip Girl. I was hooked from the pilot episode and marketing alone. I found my fashion north star in Blair Waldorf (and a bit of her attitude, though I like to think we’ve both evolved). And like many southern California 15 year-olds, I was completely mesmerized with the foreign, intoxicating glamour of New York City. I had never gotten a proper peek behind the curtain… and once I did, I couldn’t get it out of my mind.

New York became *the* goal. It was one of those daydreams that I would always came back to. I was desperate to know the version of myself who lived in the city. And at 29, I finally hopped on* the plane at LAX with a dream and (many) cardigans and made my way to Manhattan.

Manifesting… ✨

Channel your inner Uptown Girl:

If you are familiar with New York, by way of Gossip Girl or otherwise, you should know that November belongs to the Upper East Side. The marathon runners make their annual trek through the park. The fall foliage is at its peak. It’s Blair’s birthday month (suchhh a Scorpio). And everyone knows that the Thanksgiving episodes of GG are the best of the season.

So in the spirit of giving—in every sense of the word—here’s how to channel your inner Uptown Girl this month! She’s in there.

In this issue of Extra Dressed:

• SPOTTED: where to see & be seen on the Upper East Side.

• Style Muse: Blair Waldorf. What would Queen B wear in 2025? (if she was on a budget, ugh) + links!

• You know you love her: a Q&A with a past UES resident and member of New York’s literary elite, Mackenzie Newcomb

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SPOTTED: WHERE TO SEE & BE SEEN ON THE UPPER EAST SIDE

If you’re planning a trip to New York, a day and eve on the Upper East Side is a must. While this list is far from extensive, these are some of my most beloved spots in the city… especially in November.

• Bemelman’s Bar. You knew it was coming. Everyone should sip a martini over live piano in a room hand-painted by Ludwig Bemelman himself. It’s a New York institution. Glam!

• The Met. Always worth a visit. My favorite piece is Cupid and Psyche by

  Antonio Canova, it just makes me feel fuzzy inside. And yes you should sit on the steps.

• The Domino Room. A newer addition to the neighborhood but immaculate Saturday afternoon vibes. Grab a spritz and sit upstairs on the patio.

• The H&M on E 86th Street. The best H&M in the city! Not Blair-approved but that’s okay we don’t have to tell her.

• Salon 94. One of the most gorgeous art exhibits in the city, situated in a townhouse by the park. Plus, it’s free.

• La Bonboniera. Adorably chic and charming cafe meets wine bar. Grab a glass of sparkling and a hazelnut bomboloni. Nice place to go with a book or a journal… or a friend. Very versatile.

• Central Park, obvi! Everyone should see Bethesda Fountain, do a lap around the Jackie O Reservoir, and stroll through the Conservatory Garden on E 105th St.

• Butterfield Market. I’m a sucker for an artisan grocery store. Everything is fresh and beautiful and yummy. The branding is adorable. It doesn’t have the same celebrity as LA’s Erewhon, but only because it doesn’t want it.

• Sukoshi. A new asian beauty store that’s given me my three favorite products of the year. Everyone is extremely knowledgable and helpful inside. Plus it’s ~so cute~.

• Sant Ambroeus on Madison. I know it’s a chain, bla bla bla. This is the best location. Order the artichoke salad and the princess cake.

• Caffe Buon Gusto. Excellent no-frills Italian food. The vodka sauce with mozzarella is IT. Love popping in here after a Friday eve at the Met. Would be a great date spot.

• Albertine Book Store. Like stepping into another world. Books in French and English and the most gorgeous mural for some eye candy.

• The Niche Shop. Excellent curation of thrift and vintage finds, sunglasses and bags. They also pop up at the Grand Bazaar on the UWS.

• Brandy’s Piano Bar. Go here after dinner for cheap drinks, loud singing, and very New York energy.

CHANNELING BLAIR—WHAT WOULD BLAIR WALDORF WEAR IN 2025? (if she lost her inheritance, lol)

Prep school dressing, I love you so.

I was born to go to private school, forced to live in a great public school district (thanks a LOT mom and dad). I would have absolutely devoured a uniform — and tbh, I basically wear them now for fun.

I admire Blair’s styling (by way of Emmy-award winning costume designer Eric Daman, who also styled the women of Sex and the City!) because it’s both classic *and* uniquely hers. She’s a strong character and I feel like her styling choices emphasized her bold, fearless POV: colored tights, big bows and headbands and accessories, oversized sunglasses and bags, printed dresses and skirts. And while she thrives in the fall and winter, her style was equally memorable and #onbrand in the summer. Lest we not forget her iconic Hamptons white party Marc Jacobs dress!

I’ve already written about my obsession with tights, essential reading for the season if you ask me. But after years of channeling Blair myself, I wanted to share what I think she would be shopping for this season…if she lost her Black card and was a normie for the day.

Everything above is linked in my ShopMy (affiliate link disclaimer!) — but highlighting some of the pieces I love, own, and recommend from above:

1. Artizia Grey + Plaid Olive Mini Skirts, I have three of these and the quality is gorgeous and they’re a good price! Excellent length, not too mini and great to pair with tights.

2. Calzedonia Totally Invisible Tights in Black. Listen if there’s one thing you should trust me on… it’s this! These are the BEST tights on the market. They are durable, the perfect denier level (can still see leg underneath) and have a smoothing/shaping waist. I also love the wine color. They always have sales. Stock up!

3. Peche Loafers. These are the most comfortable and cost effective loafers in the world. Like butter! Plus you’re supporting a small business (they have a brick and mortar store on the Lower East Side).

4. The SoSoft Cardigan from Old Navy. I have soooo many of these. Red is Blair’s color, as it would be.

5. The stretch headbands are both adorable and good for keeping ears warm! I have some from CVS but I like the width of these from UO. A Blair roundup would be incomplete with one.

6. I bought this dress from Revolve SOLELY bc of how it was styled with the light blue tights. J’adore.

7. I gasped when I saw this bow top from GAP. So insanely Blair-coded but modernized into a 2025 version of her. Obsessed!

You know you love her! Spotlight on New York’s queen of the literary scene: Mackenzie Newcomb.

and I were introduced through a mutual friend in a text thread in 2016, met IRL in 2017 over a bottle of rosé in Central Park (how fitting), and remained in touch until I moved here in 2021—bless the internet! Now we get to be friends on and offline. When we first met she was working for Petrossian Caviar because she’s always been a woman with ~taste~ and her dreams of entrepreneurial success were just starting to take shape.

Fast forward to now, Mackenzie’s Bad Bitch Book Club has grown to 85K followers, thousands of members and has been featured in the New York Times and Vogue. She sits on the committee of the New York Public Library’s Young Lions (+ recruited me as a member!) and has taken over TikTok as the platform’s resident young, hot mom.

Mackenzie lived on the Upper East Side for many years, so I asked her a couple Qs on the famous zip code as she’s not one to shy away from sharing her (correct) opinions:

What’s something about the Upper East Side that might surprise people? The UES is definitely known for its uniformity, but it’s actually a center point for NYC culture. They have a strip called “museum mile” and you could spend your entire life exploring it without ever getting bored.

If you had to describe the Upper East Side in three words, what would they be? Timeless, comfortable, chic

How did living on the UES shape your New York experience? I loved living on the UES because it gave me such an appreciation for Central Park. In my opinion, the reason to live there is to have access to it. Also, living in such close proximity to the Met, Guggenheim, El Museo Del Barrio and the Museum of the City of New York, among many amazing galleries, really helped me foster a love, appreciation and understanding of art.

What is the real dress code of an uptown girl? Right now? Amazing vintage coats, ear muffs and big sunglasses. What you’re wearing now should be what you’d also wear at the age of 80. The old ladies of the UES are the fashion icons, and anyone under 60 is just trying to live up to their elegance. The UES and LES residents dress like they live in two completely different cities.

Describe your perfect November day on the Upper East Side: It’s a Friday. Coffee and pastries from Patisserie Vanessa & then hitting the Met just for the next exhibit I haven’t seen yet (because I’ve seen it all.) Lunch is Butterfield Market (Mandarin Salad) if it’s a warm day, we’re eating it on a park bench right at the entrance of Central Park—which we are going to bop around for a bit and look at the remaining leaves. If it’s cold, La Sandwicherie’s french onion soup instead. Dinner is at Flex Mussels and i’m ordering the Parma flavor. Doing dessert and drinks at Hoexters afterwards because there are no rules here—espresso martinis and cookies with ice cream. If we aren’t too full, dancing at Ethyls.

RAPID FIRE RECS:

• Worth the hype: Cafe Buon Gusto

• Retail therapy: Zitomers

• Bring a book and stay awhile: Cafe Sabarsky (mid-day, mid-week!)

• Local gem: Budapest Cafe, AOC East (french fries and escargot for moi!)

• For the art lover: Salon 94—a free gallery that never fails to blow me away.

Hope you enjoyed this little ode to the UES! What did I miss? Let me know where else I should add to my Google map.

xoxo ;) Caylee

Thank you for reading! If you enjoyed this post you may also love Always on brand! Easy ways to find and refine your personal style and How to romanticize your life (according to self-proclaimed experts)

Today’s edition is a collaboration between Caylee Ashwell of extra dressed, and Kayla Douglas, editor behind The Sunday Series—book club besties, downtown New York girlies, and lovers of the little things, this special send is intended to help you romanticize your life.

Two thirty-somethings walk into a bar…and immediately transform into the main characters of a ‘90s Nora Ephron movie. What can we say? We’re hopeless romantics romanticizers.

Maybe it’s because we live in New York City. Maybe it’s because we were once impressionable tweens during the romantic comedy peak of the early 2000s. Maybe it’s because we’re single and have developed a parasocial connection to the women of Sex and the City and their respective timelines. Whatever it is, we’ve bonded over our ability to romanticize our lives.

This ones for the girls who get excited about anything and everything!!!!!

A little intro:

This collab means everything to me! If you’re reading this I assume you are familiar with me and extra dressed. So, let me formally introduce you to one of my nearest & dearest friends, , a bright light in my New York life and a huuuge source of inspiration for me. Kayla is someone that does it all and makes it look effortless. She’s a 3X marathon-runner, has traveled to more countries than most could name on a map (if you’ve got a trip planned make sure to check out her coveted travel guides!), and authors three unique Substack publications, including her weekly newsletter , a platform best-freaking-seller.

She’s also the founder (!!!) of our beloved which has brought joy, purpose and community to not just its six members, but also any inspired readers that come across it online. She’s a big dreamer, baby!

The Sunday Series

Your weekly permission slip to pause and indulge—featuring New York musings, travel recommendations, books to savor, and candid Q&As.

By Kayla Douglas

Now that we covered intros, let’s dive into a warm-up? We’re lucky to live in a city that makes romanticizing an easy part of the everyday. So, we sharing some of our dreamiest spots for you to check out or bookmark for your next trip to the greatest city in the world!!!!!

What does ‘romanticizing your life’ actually mean to you?

Caylee Ashwell: I think it’s about indulging the present moment. We’re constantly being pushed towards what’s next (Anthropologie already has holiday ornaments in their windows for crying out loud), so romanticizing feels like a way to stay grounded in the now.

It’s treating the little things with just as muce importance as the big things. It’s easy to get excited about a trip that’s coming up in six months… It’s more impactful to get excited about something small every single day!

@heycaybabeIf you’re looking for a sign to move to New York, this is it. It’s as big and tough and beautiful as you think it is. This weekend was a reminder of why I love it here so much and how content I am with this little (big) chapter of my life. Feeling so lucky 💌 🍎 #romanticizeyourlife #luckygirl #nycaydates #satc #maincharacterenergy

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Kayla Douglas: Romanticizing my life is all about turning the mundane moments into memories. For me, the sensory bits—tasting the season’s first peaches from the farmer’s market, sitting on my roof to journal at sunrise as the full moon sets, walking home listening to an audiobook without scrolling—are the ones that stick with me long after they fade. So even when it comes to the less sexy moments in life (whether I’m schlepping through the city carrying what feels like my body weight in groceries or commuting across town for an inconvenient doctor’s appointment), I try to find a way to treat it all like a game.

I’m constantly stopping to take videos of vignettes that catch my eye across the street, carving out time to get a little treat to savor, or sticking my head out of a taxi to see the movie passing by my window better. For me, romanticizing life is all about noticing the small moments—because the sum of all of them ends up being your life.

How does the West Village Book Club lens fit in—where does literature meet lifestyle?

KD: West Village Book Club is made up of women who really understand the art of romanticizing one’s life. For fear of being too literal, I think the fun part is that every one of us has ‘main character energy’ in our own way—each of us is doing so much professionally and personally. So, beyond the books we read and the connection we have to those stories, we’re using this time in our early to mid-30s to maximize how we move through the world.

We’re not just voracious readers but connected by our shared desire to experience life loudly, taking every opportunity to travel together (we’ve done offsites in Montauk, Montana, Paris!) and making a point to go to concerts, art exhibits, theatre, and book events at every possible turn.

What are your morning non-negotiables?

CA: I’m more of a night owl than a morning person! So I’m pretty gentle and flexible with myself in the AM. I will say I recently started weaving in a morning meditation and it’s been a game-changer on my getting up process. Before getting out of bed, I put on my Omnilux Red Light Mask and listen to a 10-minute meditation on “what’s the best that could happen?” and proceed to spend the first 10 minutes of the morning dreaming up a life where everything goes right. It’s been a positive, grounding habit for me.

KD: I’m such a morning person! My non-negotiable is mainly just that I need at least three hours of runway in the morning before I start work. In my perfect world, I’ve fallen asleep (after reading!) the night prior by 10 p.m., so I’m up between 5 a.m. and 6 a.m., depending on my workout schedule. I love to start the day with journaling when time allows. Then, movement has to happen for me in the morning, and that’s often in the form of a class at 6:30 a.m.—lately, I’ve been loving a weights-based workout, but I’ll mix in sculpt for something lighter, too.

Afterward, I’m coming home to have a proper coffee and take a shower with whatever I’m listening to at the moment in the background, sometimes a podcast, sometimes an audiobook. Then, I’m making myself breakfast…my current hyperfixation is Siggi’s plain Greek yogurt mixed with vanilla protein powder and topped with grain-free paleo granola from Sunlife Organics. Finally, around 9 a.m., I’m walking from West Village to my office in Chelsea on the High Line!

How does your space, outfit, or soundtrack affect your creative energy?

CA: I make a playlist at the start of each season and “brand” them with fun titles and photo covers. If you are not adding cover photos to your Spotify playlists, you’re missing out on prime romanticizing energy! The music becomes associated with whatever I am doing in that moment and the songs always bring me back to specific memories. Right now it’s time to bring back Scorpio Energy and lean into the witchy, mystical vibes again but my Autumn Rom Com is one of my very favorites!

How do you use fashion or routine to shift your mood?

CA: I operate by the 2/3 Rule – Hair, Makeup, Outfit. If you want to feel put together, you need to have at least two of the three done. You never know when you could have a meet-cute on the streets of NYC; one must always be prepared to strike while the time is hot!

What’s your philosophy on getting dressed?

CA: I used to have a poster in my living room that said “I’m nicer when I like my outfit” and while I know there’s a dash (heavy pour?) of millennial cringe in that now, the statement remains the absolute truth. I operate best when I am *extra* dressed. I feel most powerful and beautiful when I am in an outfit that makes me happy. I try to add and refer to my Aspirational board on Pinterest often, esp if I need a little inspiration.

KD: To be honest, getting dressed is something that I’ve struggled with for as long as I can remember! Though increasingly, I’m finding greater ease by gravitating toward a true uniform. Basically, my dream outfit every day is a button-down from With Nothing Underneath tucked into a wide-leg jean with a belt and a ballet flat. Throw a sweater over the shoulders on colder days and voilà! Then, when it comes to going out for events or with the girls, I feel my best when I’m extra girly and polished—I love a skirt or dress moment and if terrain allows, a heel!

What’s one tiny food-related luxury that always lifts your spirits?

KD: I’m someone who thinks about eating as an act of pleasure, so every meal I consume is driven by a desire to enjoy myself. Going out to a new buzzy restaurant is a quick hit in that regard, but when I think about romanticizing my life, I actually think so much more about cooking. That starts with the provisioning of ingredients and we’re fortunate to have so many incredible grocers here in the city that carry unique products and artisanal goods imported from around the world. One of my greatest weekly luxuries is my trip to Murray’s Cheese where I buy French butter (Beurre d’Isigny with sea salt crystals), Bulgarian feta (in the brine), Spanish wild-caught tuna (Ortiz, packed in olive oil), Italian olives (Castelvetrano olives, pit in) on a regular rotation, plus whatever else strikes my fancy at the moment!

What’s your definition of a romantic solo meal?

CA: When I first moved to NYC, I had a couple-week run where the city was testing me every which way. Mice, cockroaches, a landlord who was unreachable, a broken AC unit in the middle of the summer…it was like the city was hazing me. I felt so alone and deflated. But instead of wallowing in it, I put on an outfit, grabbed my Kindle and a notebook, and walked outside to go treat myself to a nice dinner. I ended up sitting at the bar at L’Artusi and ordered the cacio e pepe and a glass of rosé. Mid-meal, Brook Shields walked in and sat next to me at the bar (she is a WV girl through and through – her dog is named Tuzi after the restaurant, lol). It was such a fun, unexpected, glitzy city moment. And it was just mine. There was power in that feeling!

KD: Since I live alone, basically every meal at home is a romantic solo meal!!! But the times when I feel most like I’m taking myself on a date are those when I go out and eat at a restaurant alone. The key for me is to always have a book in hand and really make it an entire experience. I did this just yesterday, where I dipped into Commerce Inn with our West Village Book Club October pick and treated myself to a stack of their sumptuous pancakes, eggs, bacon, and coffee. To me, that’s peak romanticizing your life–not waiting for anyone else to do what you want to do, but instead being shamelessly indulgent and present in what feels good.

What does it mean in practice to romanticize your friendships?

CA: “Nearly everything I know about love, I’ve learned in my long-term friendships with women.” That line from Dolly Alderton’s Everything I Know About Love feels like the thesis of this chapter of my life. I’m not currently in a romantic relationship, but the love and fulfillment I find in my friendships are more than enough to fill my cup. But friendships take work!

KD: In the first episode of season four of Sex And The City, Charlotte famously says, “Maybe we can be each other’s soul mates. And then we can let men be just these great, nice guys to have fun with.” This line resonated with many women because our female friendships are built on intricacies that are so entrenched in girl code. My friends are constantly checking in with each other (How did that call go? / Do you want to go see that new film in theaters next week? / OMG, I saw the café down the street is carrying your favorite brand of nutmilk now. / Let’s block that week in July again for our annual summer trip!) with a level of intentionality that feels romantic. And while we each do want that romantic kind of love in our lives, the foundation of our connection to one another will never lose its importance!!!! So, no matter what, watering our friendship garden is always going to be a priority.

Thanks for indulging us with this collab post! We’d love to hear from you in the comments with any advice on ways you romanticize the little things.

XOXO, Caylee and Kayla

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For some reason (or actually, for all the obvious reasons), the article has started trending again. And while I’m thrilled it continues to resonate, there are a few more whimsical habits that deserve to be shared!

When coupled with action, I truly believe that joy is the resistance. So, with bows and ribbon and cake on Wednesdays… we fight on:

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1. Wear slippers around the house. This was the biggest and most obvious miss from my first article. I’m a slipper loyalist. If I’m home, there are slippers on my feet. What’s more whimsical than sliding your feet into plush clouds and calling them house shoes? And I’m not talking about Uggs that you can wear running errands… Real, ridiculously fluffy slippers.

2. Compliment a stranger daily. The only thing better than getting an unexpected compliment is giving one. You have the power to positively change the trajectory of someone’s day in an instant — use it! I especially love to compliment older women I see in the city. Baddies are forever.

   A friend I admire deeply for her gorgeous, oftentimes very whimsical, life journey, recently wrote on her Substack: “Not sharing a compliment is like wrapping a gift and never giving it.” It’s true. Free love is meant to be given away!

3. Commit to a 10-minute daydream, every morning. I am ~always~ in my head. If my eyes are open, my brain is buzzing a million miles a minute and approx 99% of what’s going on up there is non-sense. I blame this on my Aquarius air-sign sun. To help calm the chaos, two of my best friends (both earth signs, worth noting) have continuously suggested I try meditation. After many failed attempts, I finally found a routine that works for me. And—can you believe!—the biggest adjustment is that it feels more whimsical. Before getting out of bed each morning, I put on a 10-minute guided meditation that asks me to envision “what’s the best that could happen?“. It feels more like dedicated daydream time. Some mornings I’m daydreaming about a love that feels like an ‘80s John Hughes movie. Others I’m walking around with Obama-era optimism and confidence in our country. One morning I spent 10 minutes thinking about my dream dog. But for the first 10 minutes of every day (for the last 15 days, my longest consecutive streak!), are spent imagining a life where everything goes right.

4. Adopt an “it’s the little things” mindset. My Pinterest has been serving me photos of at-home lattes made with ice cubes shaped like flowers, butterflies, hearts, etc. I fill my ice trays every night, whyyy on earth am I using square trays?! Naturally, I ordered some and daily drinks are exponentially happier. It really is the little things! Other little things you can do: name your plants and give them detailed background stories, subscribe to a print magazine for a monthly moment of screen-free delight, put old Disney movies on in the background (2D animation is soothing!), listen to a Nancy Meyers playlist when you’re cooking…

5. Celebrate color!!! I fear we’re in the beige epidemic. Yes, in some instances a monochromatic look is chic and clean. But when your wardrobe, your home, and your desk are all 50 shades of grey, anything in color starts to feels out of place. And where’s the whimsy in that? Everyone’s tastes are different and I’m sure my dusty pink comforter would stress some of you out, but there’s always room to add more ~life~ back into your space. Choose the colorful flowers. Wear jewelry with some gem stones. Paint your toenails Got The Blues for Red instead of Bubble Bath. Wear a berry lipstick for fall. Buy a leopard blanket to cozy on the couch with…and hide it in the closet if you don’t want it out all day. More glad, less sad.

   

6. Create more immersive content experiences for yourself. My book club is currently obsessed with The Gilded Age on HBO (thanks to my BFF ’s recommendation!). We all recently returned from Newport, RI where one of our book club members got married, so we were already enamored with the Gilded Age lore. We did the Cliff walk, toured the Breakers, and the bride’s welcome party was at the International Tennis Hall of Fame… all of which are featured in the show. But that wasn’t enough! A handful of us read/are reading books centered around this time period, too. It’s like our own Gilded Age history syllabus come to life! Everything about it felt richer. I have a trip to London coming up next month and will also be theming my content to align with my travels. Book & show recs welcome!

7. “Look for the hearts.” I listened to this Mel Robbins episode three years ago and it has always stuck with me. She talks about synchronicities and how to train your mind to spot magical moments. One of the exercises she suggests is to look for the hearts. When you’re walking around and going about your day, keep your eyes open for heart shapes. You will be shocked at how often you see them. On signs, logos, posters, graffiti, and on people’s clothes, in shadows on the sidewalk, in nature and clouds. They’re everywhere. And you could do this with anything ~ butterflies, your lucky number, a specific shade of a color, your favorite word. It’s just a practice in being aware and choosing to keep your eyes open for the good stuff.

8. Lean—the f*ck—in to the holidays. Whether you like it or not, festive season starts now! There’s no better way to connect to your inner child than to lean TF in. Wear the damn costume. Write in a gratitude journal every day in November. Drive around the fancy neighborhood and look at Christmas lights. Make a mulled potpourri pot for your stove. My personal favorite: make a seasonal craft! Be tacky, kitschy, and over-the-top simply because you can. The world feels so dark, so serious. Let this final season of the year be glittered with brevity and light. The holidays are easy and happy for some, tough and heavy for others. Wherever you sit on that spectrum, choosing to celebrate joy despite it all is an act of self-love you deserve.

9. Work from your local library. The greatest WFH hack of all time! Your local library has free WiFi, a quiet atmosphere, printer access, and overall beautiful, calming energy. Coffee shops can be so hit or miss when it comes to productivity. Libraries are much more consistent. My favorites in NYC are the Jefferson Market Library in Greenwich Village and, of course, the iconic New York Public Library next to Bryant Park.

Let’s end the year with an explosion of fun—dust off your glue gun, always take a look at the dessert menu, and don’t forget to tell your friends how much you love them.

What did I miss? Let me know your favorite whimsical habits <3

xx, Caylee

I’m a big “look for less” kinda girl. While I love a designer moment (mostly in the form of bags and dresses), a lot of my clothes are very affordable. Moving to New York and living on my own has made me poor much more aware of my spending habits. They say you step outside your apartment in NYC and spend $100… and that’s if you’re lucky!

I frequent thrift stores and vintage markets, shop on Poshmark and eBay, have tried every rental company under the sun [fun fact: I was on Rent the Runway’s billboard in Times Square and it was the coolest thing ever]… but I also populate my closet with affordable pieces from Gap, Old Navy, HM, Uniqlo, Muji, etc.

Fast fashion has plenty of negative ramifications, so this isn’t a message about blind or excessive consumption. But there are ways to look and feel your best without always breaking the bank. Through my own trial and error, I’ve created some ground rules for shopping affordable pieces to make sure they look much more expensive than they are. Since we’re about to dive into fall, I thought I’d share my tips with with you… and compile a curated selection of my favorite $50(ish) or under finds for you to shop (a paid subscriber exclusive!).

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THE GROUND RULES:

Always go to the thrift store or flea market first. Thrifting takes patience and practice! Never enter a thrift store in a rush, you will be disappointed and overwhelmed. Always go in with ideas in mind, it helps to keep your eyes focused for specific items. I especially love vintage shopping for coats. All four of my favorite coats below are from second-hand shopping and made from high-quality material, are warm and durable, and unique!

Bargain basics should come in “basic” colors. If there’s one learning you will take from this piece, let it be this! It’s much easier for affordable clothes to look high-quality when they’re in a neutral or standard color… and this is coming from a very pro-color girl. Stick to your basic neutral or standard color palette — like a true red or a deep navy— and accessorize with other colors and prints.

On that note… be weary of florals. Cheap floral fabric is a dead giveaway for quality and cost. A lot of time the fabric is cut and sewn in the back but the print is misaligned. For prints, I like to stick to simple designs like polka dots, stripes, gingham, etc. But as always, there are exceptions to the rules! I got an incredibly vibrant orange duster from Target a couple years ago and its one of my favorite items. It just worked.

Trendy vs. timeless = save vs. splurge. There are items that are always worth a splurge and some things that never are. Can you see yourself wearing it in a couple years? If yes — splurge! Is it a very time-stamped item? Save! Some things that worth a splurge to me: anything deemed a ‘classic’ like ballerina flats, trench coats, and cashmere sweaters, jeans that fit perfectly, winter coats (regardless if bought new or second-hand), heels you will wear to events and weddings, one-of-a-kind pieces like handbags and evening gowns. Some things I would save on: anything that feels very ‘of the times’ like 2025’s mesh flats and split button vests, white kick around sneakers, T shirts, layering tanks, long sleeves.

Focus on silhouettes you know look good on you. I typically don’t take huge risks when shopping affordably. The cut of a T shirt, the cinch of a waist on a sundress, the rise of a pair of jeans… stick to what you know and love. Look at your favorite, most worn items in your closet and buy affordable pieces that hit your body in the same places. If you don’t like how you look in an expensive A-line dress, you probably won’t like it in a cheaper alternative.

Pair it with something luxe to tie it all together. The track pants below are from Amazon (purchased pre-boycott) and both outfits are great examples of high/low dressing. The daytime outfit had a royal blue sweater from Free People and nice sneakers to sandwich the casual pants. The nighttime outfit is one of my faveees of all time. The top is Sandy Liang ($350, but rented via Rent the Runway) and the shoes are from Zara. Not pictured: my beloved Chanel. I think the reason why this works is because of the mixture of high-quality pieces when it counts: the shirt is beautifully tailored and the bag is a timeless luxury piece. It makes elevates the pants and shoes.

A little extra* for paid subscribers <3

Moving forward, a few sections of my newsletters will be exclusively for paid subscribers. I am so0o0o0o appreciative of the engaged community we are building here, so everything that lives behind the paywall will be especially curated. Think more shopping and styling, guides and resources, deeper thoughts and musings, etc. Please leave a comment what you want to shop/see more of/chat about!

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K, LET’S SHOP:

If there’s one thing I can convince you to buy on this list, let it be Old Navy’s

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Something very important to know about me is that I ~*always*~ ride for the girls. At dawn of course, but also at quite literally any other time of day. For me, there is no source of inspiration more powerful than a creative woman who’s doing exactly what she was meant to do.

I’m lucky enough to have many of these women as inspo IRL (hi, Mom!) and as large pop culture figureheads (hi, Dolly!) but the women I want to share with you today exist in the in between. I’ve fallen in love with them their work the modern way: on the internet.

These woman feel like my own personal influencers. Not necessarily in a sell-you-something kind of way, but in an inspire-you-to-do-something kind of way. Artists, designers, writers, stylists, activists, or multi hyphenates of all the above, that I’ve followed and referenced for years. After putting together this piece, I tried to discern what connected them and why their specific journeys mean so much to me. They’re all creatives, yes, but more than that they are risk-takers! They’re bold! They’re dripping with originality! And perhaps most importantly of all, they all make the world a more beautiful place. Magic.

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MEET THE MUSES:

Charlotte Beecham of Charlotte Simone:

Show me the coolest girl in London and I guarantee there’s a Charlotte Simone hanging in her closet. The first Charlotte Simone coat that ever tickled my eyes was the Pink Penny and god—I wish I bought it right then and there. As quoted on her website, “(Charlotte’s) designs are heavily inspired by nostalgia, womanhood and vintage silhouettes.” Though her styles feature oversized collars, fur-trimmed cuffs, animal prints, and various shades of pink, they feel classic. I don’t know how, but she makes a leopard print and pink fur-trimmed jacket look timeless, not trendy. All of her pieces are made to order in drops, amplifying their cool given their limited production numbers. Her belief is to create less, but better and given the fact that I’ve been lusting over them for years I’d say she quite excels at that. Talk about extra f*cking dressed.

stay inspired by Charlotte: charlottesimone.com | @charlottesimone

Christina Grasso of The Pouf:

One of my first proper internet crushes. I stumbled upon Christina in the early Insta days… back when Glossier reigned supreme and everything was still fun and cool and millennial pink. At the time of discovery, Christina ran Style Caster’s Instagram and her cheeky captions, clever pop culture references and exquisite taste seeped though the brand’s grid. But that was years ago, now she’s running her own.

Christina has meticulously crafted her personal brand in a way that multi-million dollar companies and creators alike could only dream of. Many online personalities (both brands and people) are dictated by what’s trending, often sacrificing authenticity for views and impressions. But Christina has always had an ironclad POV. She loves Stevie Nicks, roman noses, nuns, gloomy weather, wearing all black despite the season, red lipstick, MK&A, candelabras, and high fashion. Always has, always will.

She’s had multiple viral creative content ideas that brands and creators have since stolen been inspired by and I wouldn’t be surprised if one of her creations are saved on your phone right now.

Stay inspired by Christina: | @thepouf

Aurora James of Brother Vellies & The 15% Pledge

When I think about Aurora James the phrase that comes to mind is “her beauty is the least interesting thing about her”—and goodness, she is beautiful. I was introduced to Aurora in 2020 when she founded the 15% Pledge, a non-profit organization that aims to close the racial wealth gap by encouraging retailers to commit 15% of their products/SKUs to Black-owned businesses. What started as a big, hopeful idea has turned into successful partnerships with powerhouse brands like Macy’s, Sephora, Nordstrom, and Ulta Beauty. Pretty major! And that was her second endeavor…

Aurora is also the founder and creative director of Brother Vellies, a luxury shoes and accessories brand with some of the most unique and fabulous pieces you’ll ever see. The company’s goal is to keep traditional African design practices & techniques alive while also creating and sustaining artisanal jobs. The story of its inception is beautiful and cosmic. I recently listened to her memoir, Wildfower, and was charmed once again by her curious mind, strong sense of self and commitment to making the world better… in many aspects of the word.

Stay inspired by Aurora: @aurorajames | @brothervellies | @15percentpledge

Alison Bornstein — Three Word Method:

Alison fundamentally changed the way that I approach fashion. I’ve spoken about her Three Word Method before as it’s been helped shape my own personal style and relationship to shopping. Alison speaks confidently about style in a way that’s aspirational and accessible all at once. If you want to get to know her thought process I highly encourage you to watch her Three Word Method series on TikTok. It’s a rabbit hole that will leave you entertained and inspired.

Another styling tip she’s coined is the Wrong Shoe Method. Essentially, if you want to add interest to your outfit, choose the shoe that doesn’t quite make sense. One of my favorite outfits I’ve ever worn was heavily impacted by both of her styling methods and I remember feeling soooo confident and comfortable all night. I loved the way the clothes made me feel and I wouldn’t have been so brave to pair them together had Alison not laid it all out to me.

stay inspired by Allison: |

Read more about the Three Word Method here:

Blair Breitenstein Williams of Blairz

My favorite artist and illustrator. I love the way Blair sees and depicts women, always sure to accentuate their most feminine features with flirty lashes, pouty lips, and sharp, but still soft angles. I wish I could see the year I followed her on Instagram, because I’ve been a quiet champion of her work for many years. For much of my life her work was out of my budget (rightfully so!), but I always knew I wanted one of her illustrations in my big girl apartment, whenever I got one. Luckily for me, she decided to do sidewalk sales in Soho this summer and I finally got to meet her in person and get my Blairz original (on the left above).

I’ve been trying to lean more into more 1960s styles and silhouettes and Blair’s art has intrinsically influenced that. A reminder - all art and creativity is connected!

stay inspired by Blair: blairbreitenstein.com | @blairz

Gabby Whiten | Oh Eight:

Gabby is making the 2000s romcom female lead role of big time magazine editor a reality… but her mag is her Substack and she’s the EIC. Remember going to the airport and picking up a magazine to read on the flight because you either 1) didn’t have a phone (take us back) or 2) it didn’t have wifi? Those are the vibes of Oh Eight. Its namesake is actually inspired by the nostalgic bliss of that magical year and ‘the glossies’. I love the way she catalogues her thoughts and the mood boards she makes to accompany her words. Her weekly newsletter is quippy and light, but always intentional. She has her finger on the pulse of everything cool, so if you want to be in the know, subscribing to her work is a good place to start.

stay inspired by Gabby: | @gabbywhiten

Dolly Alderton:

Everything I Know About Love came to me exactly when I needed it—30 years old, still new to New York, and deeply conflicted about the relationship I was in (spoiler alert: you shouldn’t be deeply conflicted about the relationship you are in, lol). Her memoir on parties, dates, friends, jobs, life, love was like a peek into my own brain and a big inspiration behind my desire to write extra dressed. Who doesn’t want to read someone else’s diary?!

Aside from her wit and charm, what draws me to Dolly most is her love and appreciation of women. You can feel it in every word she writes and you can see it in every outfit she wears. Dolly is a girls girl. And as you know…that is my kinda girl. She recently adapted Pride & Prejudice for Netflix, so I expect we will be seeing a lot more of her!

stay inspired by Dolly: @dollyalderton

Sophie Cohen & Jess Habich:

A newer girl crush duo of mine are best friends Sophie Cohen (@styledbysoco) and Jess Habich (@jespressobean). Some women just KNOW how to style. I aspire for my clothes to look as effortless as theirs do. I am coupling them together because they are BFFs and are always seem to be “Mary-Kate and Ashley matching”, whether intentional or not. MK&A matching is basically the phrase same, same but different come to life. Unique on their own, even better together.

Sophie’s commitment to pink puts mine to shame and I’d say I am I’m pretty loyal to the color. She inspires me to mix prints, that Chanel ballerinas are always a worthy investment, and that our beloved pink is a neutral if you let it be.

Jess has a beachy element to her outfits that, as a California native, I will always love. Her Montauk wedding was expertly styled and honored all parts of her: glam, coastal, feminine, sexy…but at the center of it all: cool. It seems like a lazy word, but trust me, it’s the right one.

stay inspired by Sophie: |

stay inspired by Jess: | @jespressobean

And now I have to ask… who are the creative women who inspire YOU?

xx, Caylee

Once in a blue moon, a seemingly simple quote, phrase, lyric or otherwise comes across my desk and rewires my entire psyche. Dramatic, but true. For some reason the string of words holds a truth I didn’t know I was looking for and scratches my brain just right.

And it’s always kismet. I’m never searching for the words; instead, they find me at exactly the right time—no sooner than when I’m ready to hear them, no later than when I need them most. A few weeks ago, I stumbled upon one of these messages.

I was in a funk. An unwarranted, weird, dark headspace that was completely my own doing. The voice inside my head would oscillate between sharp and bitter (comparison kills!) to melancholic gloom (is there ever anything good on the news?). Everything just felt icky. And for some reason I just kept wallowing in it.

In the midst of this dark cloud, I opened my phone for the 4,756th time (helpful!) and the algorithm served me a video so perfect, my sense of existential dread and self-loathing was cured almost instantly.

In the video was a cool girl in a cool outfit, walking through a crowded bar with the bouncy, carefree confidence of someone who has it all. A Fleetwood Mac mashup played and overlayed on the video were the words:

you can always just decide that you are so back.

I watched it over and over again. The simplicity! The truth! It was like she (cool girl) reached through the phone, grabbed my shoulders and shook the life back into me: GET IT TOGETHER, GIRL, THERE’S FUN TO BE HAD.

It was a gentle reminder from the ~uni~ that you control your happiness; you write your own reality. There are a million things that are out of your control but your reactions, your mindset, and your perspective are always yours to manage and create. I was choosing to look for the negative and let it consume me… how totally embarrassing is that?

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Meet the mantras.

Reading these simple, silly words on TikTok, and having such a strong reaction to them, made me think about the other quotes that have left a big impression on me. There are three that standout and have since become personal mantras. They help shape my decision-making and keep me grounded. I find comfort in their meaning, knowing that if I follow their direction I’ll remain on the right path!

Maybe you have one of your own that you’re thinking about right now. But I’ll share mine with you here—just in case you need a little inspo:

She who dares wins | A reminder to be brave and live loudly. I saw this quote when I was in college and it set the tone for my entire 20s. I was craving adventure and unique experiences. It helped me find the courage to live in different countries, move to different cities, make friends around the world, and generally take risks and put myself out there. I also deeply resonated with POV being ‘she’—it felt personal.

Luck favors the prepared | A reminder to be ready for the best possible outcome.

My Dad told me this often when I was growing up. There are many iterations of these words, including Louis Pasteur’s “chance favors the prepared mind” and the title of Ina Garten’s delightful memoir, Be Ready When the Luck Happens. But the sentiment is all the same: luck is only lucky when you’re ready to capitalize on it. Otherwise, it’s a missed opportunity.

Respond to every call that excites your spirit | A reminder to honor your dreams and desires.

My favorite quote by Rumi. The first time I read it, I instantly thought of New York; a place that had always pulled me in this deep, unshakable way. As a California girl, NYC felt foreign and glamorous and important. The only place that mattered! The center of the universe! Reading this validated my feelings and filled me with a sense of purpose to respond to that call. Not as a frivolous thought, but as an intentional act of self-discovery.

What are your mantras? Plz share below.

Practicing what you preach.

A week or so after deciding I was, in fact, so back, I had a perfect Sunday that only so back me could have had. When I left my apartment I saw a LaMarca prosecco poster on the liquor store across the street that read “What’s the best that could happen?” And I swear by acknowledging it, I set off a cosmic series of fortunate events & summoned all the goodness in the world.

I took an e-bike from downtown Manhattan to the Upper West Side along the West Side Highway, one of my most cherished city activities. Instead of wearing workout clothes, I put on this poofy polka dot dress and threw some biker shorts on underneath. Something about the day felt like it warranted a proper outfit, regardless of practicality.

I put on a playlist of feel good songs and began my ride. Despite a road closure and 20-block detour, I kept on my merry way and not-so surprisingly ended up exactly where I wanted to be. I went to my favorite flea market (The Grand Bazaar) and gasped when I saw the most gorgeous pair of vintage Prada heels. Of course, they were in my size. I walked to Central Park to read my book and sat next to a puppy named Lola, the same name as my childhood dog. I walked all the way home, gleeful and grateful that the flashing lights of Times Square were part of my casual Sunday commute. Inner child bursting!

It felt like all my mantras had worked together to bring me to this (seemingly ordinary) moment. She dared and she’s winning! Luck favored her preparedness! The call that excited her was worth the response! She was sooo back.

xx, Caylee

This is what democracy looks like. This is what democracy sounds like.

I attended the No Kings march in NYC and my chest swelled with a sweet, familiar feeling that hadn’t bubbled up in a long, long time: hope. 50,000+ people took to the streets of New York, despite the constant stream of rain, to show their love and concern for our country. It was powerful and necessary and invigorating. And every single person who showed up made an impact.

Despite living in what feels like the hottest political climate on record (everything’s relative), it’s easy for things to feel cold, dark, and gloomy. But I find that action—no matter how big or small—is the energizing force that moves us forward. It’s that me, espresso!

Since the election was called in November, I’ve made a handful of changes in my daily life that make me feel good. Small, but impactful things that give me power, fulfillment and a sense of peace… even when it feels like the world’s on fire. Remember, doing something is always better than doing nothing. If every protestor at the No Kings march had decided that their presence was not needed, we wouldn’t have had an 11M+ person turnout and showed the world we’re fighting back. You are important!

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LITTLE ACTS THAT MAKE A BIG DIFFERENCE:

1. Shop local. I deleted my Amazon and let me tell you—that was a hard breakup. We’re so accustomed to immediacy and excess that removing it from my day-to-day was much more challenging than I expected it to be. But I was eager to reduce the amount of money I was giving to mega corporations and funnel it into my local community. I live in an extremely walkable city with speciality stores on every corner, so this is much easier for me than it is for others. But being more intentional with where your money is going and putting it back into your ecosystem is any easy way to feel good and support your people. Disclaimer: I did subscribe to Prime Video to stream Overcompensating and it was worth it, kid!

2. Donate to friends’ fundraisers. Whenever I see a friend share a link on social media that’s raising money for a cause, I donate immediately. I started doing this during COVID (the 2020s have been eventful, no?), but it’s a habit that has stuck with me. Donate as little as $10 and skip your coffee the next day.

3. Balance your news intake. The key word here is balance. Balance doesn’t mean ignore entirely. If you are able to completely tune out the noise, please recognize what a privilege is to not have to worry about what’s going on in the world around you! Balance also doesn’t mean that the news is always-on the TV or flooding your social feeds. There are tons of daily news podcasts or email newsletters that you can add to your routine to stay up-to-date without burning out. I personally like to listen to Up First from NPR. They cover the 3 major news stories you need to start your day. NPR is an independent, non-profit media organization and is currently under threat of being defunded (classic), so I like to give my time to their organization.

4. Audit your social media consumption. Your views give creators money. Be cognizant of the lives and voices you’re funding! Want to know a secret? I use the block button a lot. It’s a harmless action that protects my peace (and my feed) from the hate we can get sucked into online. And this isn’t just political takes or hot personalities. I unfollowed Revolve on IG years ago because they posted a million times a day and constantly seeing tiny models in new clothes made me feel icky. I was in a constant state of comparison and once I unfollowed their account, it cut a lot of the negative noise. The same goes for podcasts... I’ve said goodbye to a couple long-time listens. I bet you know which ones they are, lol.

5. Attend marches and rallies. Giving your time and energy is a sacrifice and a way to show up for those around you. These can be extremely powerful and comforting, but not without a dose of uncertainty that things could get heated. My suggestion is to go with friends, consciously stick together, and walk on the side of the march rather than in the center to avoid feeling claustrophobic.

6. Volunteer your time. There are tons of ways to volunteer your time: walking dogs at the local shelter, playing bingo with seniors, making sandwiches or putting together care kits, park clean-ups, the list goes on. Commit to volunteering at least once a month (or even once a quarter) as a way to play a more active, positive role in your community.

   Some organizations I’ve worked with in NYC:

   Bright Light

   New York Cares

   God’s Love We Deliver

7. Educate yourself on local elections. When there’s a lot to do or I am feeling overwhelmed, my Dad always asks me: “How do you eat the elephant? One bite at a time.” Strange picture, yes. But the sentiment is always true. You can only tackle the big thing by breaking it down into action-oriented smaller ones. This is how I view local elections. If you want to see change up at the top, you have to start making changes at the local level. There are tons of resources that help you understand your ballot, but BallotReady is where I always go.

I strongly believe that the sexiest thing you can do in 2025 is ~give a damn~ !!!! Being an active member of your community, your country, and the world is a beautiful luxury and I hope this inspires you to make even the tiniest change… doing something is always better than doing nothing.

xx Caylee

I had just gotten my driver’s license and my parents veryyyy generously gifted me the car of my teenage dreams: a black ‘05 Toyota 4Runner, complete with a bedazzled license plate cover. It’s important for you to know that I wanted a 4Runner because Lauren Conrad drove one on MTV’s Laguna Beach. I thought there was something so California cool about a girl in a big SUV.

The summer before junior year felt like standing between two worlds. Driving brought a newfound independence, but everything was still wrapped in the simplicity and sweetness of being young. My love language was making burned CD mixes, my biggest concern was checking the progression of my tan lines, and I had a Blackberry!

That’s the kind of summer I want to have. Impossible to recreate in its entirety given the obvious, like Obama was about to be president and I had a curfew… but the essence is what I want to embody.

A summer that actually feels like summer.

Inspired by the hundreds of magazines I flipped through on the beach, this special digital mag edition of extra dressed is meant to evoke feelings of nostalgia and delight and inspire you to live a summer that actually feels like one, too.

In this issue:

• THE RULEBOOK: How to Create the Summer of your Dreams

• Style Muse: Summer Roberts. What would she be wearing ing in 2025? (+ links!)

• WATCHLIST: Take Me Back to Yesteryear… A round-up of the best 80s & 90s movies for care-free, cute, nostalgic watching. And I promise these are not the blockbusters you’ve heard of!

Editor’s Note: Some of my upcoming articles will contain guides, lists, links and insights that will be for paid subscribers. As I continue to grow extra dressed and give it the eergy it fabulously deserves, a handful of my content is going to live behind a paywall. Subscriptions start at $7/month or a little over $6 if paid annually!

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OK, let’s get to it:

THE RULEBOOK: HOW TO CREATE THE SUMMER OF YOUR DREAMS.

1. Make a list of a handful things you actually can and want to do. Once you have the list solidified, write it down or print it out on a piece of paper. Decorate it and hang it on your fridge! Check things off as if they’re as important as sending those emails…because they are. The only way your summer is going to feel any different than the rest of the year is if you intentionally make it so. P.S. Paid subscribers will be getting access to my summer idea bucket lists v soon! Comment below if you want in.

2. Once your bucket list is solidified, leave room for spontaneity. While my summer is already peppered with a handful of weddings and a few weekenders, I am leaving a lot of room for the unknown. The on a whim magic that made teenage summers so delicious was that it happened by chance. Don’t overbook yourself too soon… and as a serial planner, I’m already trying to keep my word on this one.

3. Keep track of your favorite moments, however big or small. I have a note on my phone that’s titled THANK YOU, MORE PLEASE. In the note, I write down little moments/things/interactions that spark joy. It’s a way for me to express gratitude for the moment and let the universe know I would like some more, please! A peek into the list: I found a dress on Poshmark that I’ve wanted for 3 years and the seller accepted my lowball offer, I pulled the most amazing card from a Tarot Card deck… What will you look back on and smile about this summer?

4. Treat compliments as your currency. I read a quote forever ago that says: If you see something beautiful in someone, speak it. I try to put that into practice every day. Think of giving out compliments as your summer energy currency. You’ll be a more active participant of your community, engaging with the people who share your places and spaces, and always looking out for the good stuff. And if it’s true what they say, that what goes around comes back around, then all that goodness is going to find its back way to you, too.

5. Stay extra dressed. Idk about you, but my summer rom-com main character sparkle is not turned on when I am in workout clothes with my hair slicked back. This summer, wear the outfits your older self will look back on with pride and envy. Let’s keep the skirts mini, the heels high, and the hair done. What would you want to be wearing if you knew you were going to have the best day of your life? Exactly.

   If you need some help in the styling department, read this:

6. Refresh your dating profile. I recently looked at my Hinge profile and was like… WHO IS THIS GIRL? I felt 0 connection to the curation of myself I created. So I re-did the whole thing and if anything, it’s been wayyy more fun (and active). Less soft smiles, more personality, and the prompts are less serious and easier to answer. You gotta give them a bone and make it easy to bite! One of my prompts is: The best way to ask me out is a… cheesy (but charming) pick-up line. And just like that my inbox is flooded with cheesy (but charming) pick-up lines. Good boys.

7. Find your signature something. Get a new perfume for the season. Wear only yellow nail polish. Listen to an album on repeat. Find your perfect, niche drink order and try to find the best one in the city. Pick up a new weird phrase and say it excessively. Take up a new hobby. Get bangs (…I actually strongly recommend against this but you get the point). What will define this summer for you? Branding the moment makes it more fun and much more memorable. Summer ‘08 is marked by Forever by Chris Brown (before he was dead to us!) and low rise Frankie Bs.

8. Consume nostalgic & care-free content. You are what you consume, so make it cute! See below for my round-up of movies all take place in that romantic time before we were all glued to our laptops and phones. They’ll melt your heart, calm your nerves, and give your eyes some new candy and inspiration.

9. Hot is a mindset (and also an act of self-love). One thing that is not possible to recreate from summer ‘08? My bodyyyyy. And it’s been 17 years so like, no shit? But this summer I want being hot to be an active self-care practice. I feel unstoppable with a good outfit on, a grateful attitude, some endorphins from moving my body, and a clean + tidy space. When my shit is together, my hottest and most confident self comes out to play.

10. Live that #noworries lifestyle. A few days after a particularly dramatic breakup with my college boyfriend, he posted an Instagram with the #noworrieslifestyle in the caption. Excruciating at the time, absolutely hilarious (and ick-inducing) now. It’s since become a phrase my friends will say to each other when talking about Peter Pans. But as I look to the summer I am trying to create, the saying kind of… (for lack of a better word) slaps? My friend and I were recently chatting over coffees in SoHo about how we needed to chill out a little bit when it comes to dating! And planning! And overthinking! So if you find yourself in the same boat, maybe #noworrieslifestyle can be your centering mantra, too.

CHANNELING SUMMER—WHAT WOULD SUMMER ROBERTS WEAR IN 2025? (+ LINKS!)

Every summer needs an it girl, a muse… and mine is Summer Roberts. Marissa Cooper might be considered the queen bee of The OC, but my heart always belonged to Summer. Beneath her Juicy tracksuits and layers of lipgloss was a force of a woman who knew exactly who she was and was never afraid to be just that.

On the outside she was self-assured, confident, and spicy, but at her core she was a fiercely loyal and protective friend and soft, romantic lover girl. Summer is proof that you can like shopping, tanning, and celebrity gossip and still be full of depth and empathy! We love a multi-faceted icon. She’s a perfect reminder to stay true to the things that bring you joy and who knows, maybe that’ll lead you to falling in love with a Seth Cohen type… Are you there God? Its me, Caylee.

What would Summer Roberts wear in 2025, you ask? Really cute stuff. I rounded it up and you can shop the Summer Roberts Edit here.

TAKE ME BACK TO YESTERYEAR.

One of the best things about having a young (hot) mom who grew up in the 80s is the arsenal of absolutely perfect media she exposed me to. Can’t Buy Me Love changed the trajectory of my 8-year-old life. I needed to be Cindy Mancini! All of these movies bring out those warm and fuzzies and most of them have soundtracks that often make my Spotify Wrapped.

• Can’t Buy Me Love: Nerdy boy (baby McDreamy) pays hot cheerleader to date him… one of the most iconic outfits in film happens here, too

• Now and Then: Four besties reflect on the summer that changed their lives. Really sweet for a girls night

• That Thing You Do!: Life of a one hit wonder band in the 1960s. Love this soundtrack sm.

• Empire Records: A blissful day in a 90s era record shop.

• Dazed and Confused: The first day of summer in 1979. Absolutely no notes on this film. Likely would be a Letterboxed Top 4.

• Say Anything: The iconic boombox scene and an unlikely high school romance.

• Girls Just Wanna Have Fun: A baby SJP wants to dance on national TV but her strict parents won’t let her. If you watch SATC, you’ll looove.

• Teen Witch: A little witchy magic. Reminds me of a Disney Channel original.

• Sixteen Candles: I had to include one with Molly. The male lead is very Jacob Elordi, no?

• Jack: This one might make you cry. But in a heartwarming way. The most underrated Robin Williams movie (RIP <3)

• Troop Beverly Hills: I never wanted to be a girl scout until I saw how they did it in Beverly Hills.

• Heathers: Dark comedy and camp. It’s like Gossip Girl and Scream Queens had an 80s baby.

• Clueless: I couldn’t not include it! The most impactful fashion movie of my life.

• Grease 2: As someone who wrote John Travolta fan mail because I was in love with Danny Zucko… trust me when I tell you, this sequel is incredible. Peak Michelle Pfeiffer.

Hope you loved this special edition of extra dressed. If you enjoyed this piece, please consider becoming a paid subscriber for access to more exclusive ~*best summer ever*~ content to come!

Happy summering.

xx Caylee

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I am a spring.

Spring is romantic, like transitional seasons are. But spring’s romance lies in the future nostalgia of what will be, while fall’s romance lies in the nostalgic reflection of what was.

To live for the hope of it all might be a lyric from ‘August’, but it’s written from the perspective of someone looking back. Back when things were still changing for the better! It’s emblematic of how the start of April feels to me. It’s hopeful.

As a southern California native, I never understood the triumph of spring or the beauty of seasons in general until I moved to the East Coast. There’s something inherently human about surviving the cold and celebrating the warmth, then surviving the heat and celebrating the cool… together. It’s communal. A constant stream of 70-degree days is undoubtedly good for the psyche, but doesn’t connect you with your neighbors the same way enduring the seasons does. After getting a taste, I’m not so sure I could survive without them!

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When I experienced my first spring in NYC, I was in awe. So many little moments of hope, joy and color were popping up around me. Now every year I look forward to those seasonal love letters:

• The first unseasonably hot day in late March or early April is euphoric. Everyone emerges from their winter dens and flocks to parks and patios wearing shorts and dresses. Pale skin out, desperate for vitamin D. I love seeing people close their eyes and turn their faces to the sun, hoping to take in as much of its shine as possible. It’s a fleeting few hours, but some of the best hours of the whole year. We are merely plants.

• When the city changes out its planters from winter greenery to budding tulips and daffodils. It’s a moment you might not notice unless you live in the city and are familiar with the streets and neighborhood parks. The tulips eventually become unruly and overgrown, spilling out bursts of pink and yellow and red petals.

• The best place to drink a spritz is on a rooftop, especially when it’s finally reopened for the warm weather season. Taking in the view of the skyline, from a perspective you haven’t seen in a while, never gets old.

• Seeing everyone take advantage of even the smallest pockets of nature. Yes, it is the concrete jungle, but there are thousands of green spaces waiting for you to enjoy them once again.

• The day you decide it is time to officially swap out your closet—oh, what a glorious day it is! Tucking away the coats and hanging up the sundresses and skirts is a great, great day.

• Walking down the street and seeing the most vivid puffs of pink cherry blossom and magnolia trees against brick buildings will always take my breath away. You never know when you’ll stumble upon something in full bloom!

Spring is nature’s way of saying—ONWARD! Even the dreariest winter won’t last forever, spring will always follow and welcome you into her embrace. An extra* meaningful metaphor as we emerge from one of the darkest and most unsettling ‘winters’ we’ve had in a while. Maybe ever.

I operate best when I have a quote or a mantra to guide me through the season of life I am in, and there are so many that speak to spring:

• “You can cut all the flowers, but you cannot keep spring from coming” - Pablo Neruda

• “It is spring again. The earth is like a child that knows poems by heart.” - Rainer Maria Rilke

• “There are always flowers for those who seek them.” - Henri Matisse

• “When spring came, even the false spring, there were no problems except where to be happiest.” - Ernest Hemingway

Take a moment to welcome the sunshine, the color, the warmth, and all the hope on the horizon! Things are incredibly heavy, but at least in this moment, they’re a little lighter. 🌷

xx, Caylee