You know you love me! How to channel your inner Uptown Girl
November belongs to the UES.
Before reading, please open the Spotify playlist below. We’re going for a sensory experience today:
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
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:
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.
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!
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).
The SoSoft Cardigan from Old Navy. I have soooo many of these. Red is Blair’s color, as it would be.
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.
I bought this dress from Revolve SOLELY bc of how it was styled with the light blue tights. J’adore.
I gasped when I saw this bow top from GAP. So insanely Blair-coded but modernized into a 2025 version of her. Obsessed!
Tights are cool (& sexy), don't let them intimidate you
Tights are a deeply misunderstood accessory. Fashionable, functional, and versatile; they’re a triple threat. When styled correctly, they can add depth, intrigue, warmth, playfulness, and sex appeal to any outfit. Don’t let them intimidate you.
You know you love her! Spotlight on New York’s queen of the literary scene: Mackenzie Newcomb.
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
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THIS !!! The nostalgia is dripping from this article and I am so hear for it. Grateful that I got to know you in the earliest of your Blair era and even more-so see the manifestation realized over our martinis at Bemelman’s Bar. Thank you for the vibes, the tips and magic.
loooved this!!! xoxo