Actually, it is all fun and games! How to have a summer that actually feels like one.
Like flipping through a gossip magazine on the beach.
If I could relive one summer, it would be the summer of 2008.
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!
OK, let’s get to it:
THE RULEBOOK: HOW TO CREATE THE SUMMER OF YOUR DREAMS.
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.
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.
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?
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.
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:
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.
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.
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.
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.
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 Kayla Douglas 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
this is perfection! I felt like I was flipping through a magazine from my childhood
SHE DOES IT AGAIN. This has me feeling all types of Summery ways!