After spending a summer in New York City, you realise that not only are the fashion set of the Big Apple exceptional at dressing, but there are a multitude of fashion subsets to pull inspiration from. Upper East Side style is undoubtedly one of the most iconic.
Though I can’t say I’ve watched many episodes of Gossip Girl (this may be a crime), having lived in New York, I too frequently sat on the steps of The Met with friends to do plenty of people-watching, taking in the uniforms of the suburb’s best-dressed. (And yes, I did come across a few real-life Lily Basses.) For my literary friends, it’s the backdrop of Sylvia Plath’s The Bell Jar and where Holly Golightly from Breakfast at Tiffany’s lived. It’s where Joan Didion once resided and wrote. From wandering its 37 blocks myself, I quickly learned that this area certainly lives up to its high-fashion reputation.
Like much of New York City, the Upper East Side fashion sense is renowned. Its streets hold a long history of luxury retail and fashion. It’s home to none other than iconic shopping epicentre Madison Avenue, after all, and it has held this sartorial charm since the early 1900s. Running alongside Central Park, the UES contains an immense number of impeccably dressed folks clacking in heels, adorned in stacks of jewellery and carrying the most beautiful handbags.
You’ll notice their propensity to spot trends and wear them in the most spectacular of ways. Just when you’ve settled into leopard or zebra print, you’ll be convinced by an Upper East Sider to give Dalmatian spots a try. They’re perfectly fluent in styling long-standing wardrobe staples, too. From straight-leg denim to top-handle clutches, you can always count on an Upper East Sider to serve the perfect lesson in wearing either.
If your style leans classic, or if you simply appreciate learning a few tricks from some of the most fashionable people out there, turn your attention to these seven trends from the Upper East Side that you can implement in your own rotation.
7 Upper East Side Style Trends I’m Copying in 2026
1. Tomato Red
Style Notes: Though quiet luxury and neutral colour palettes often take over the wardrobes of the most fashionable people—Upper East Siders are no strangers to trying vibrant colours and patterns and making them look infinitely gorgeous. Tomato red is one such hue that stands out from a sea of cream, black and navy. I’d try something similar to New York-based fashion editor Coco Schiffer’s look, and mix two colours that seem unexpected but look wonderfully cohesive and complementary (tomato red and chocolate brown).
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The ruched sides make this top look so elegant, but it still feels fun thanks to the bold red hue.
Natural materials like linen and hemp can look both laidback and ultra-polished, and a crisp button-down helps with the latter.
Just the slightest pop of red for more minimalist looks.
For summer nights enjoying sips on a rooftop bar in NYC, this dress is superb.
2. Top-Handle Clutch
Style Notes: As a fashion intern living in New York trying to find my way, I encountered a very stylish high-ranking magazine editor in my office stating that canvas tote bags were a no-go and structured handbags were everything. She wasn’t wrong—though I’ll always love a canvas tote—especially when you’re looking to make an outfit feel more elevated. A top-handle clutch with a structured shape is exactly the type of accessory you need for continued elegance. Just look at how this shape has saturated the luxury market, from Hermès’ Kelly Pochette to Bottega Veneta’s Andiamo bag to Savette’s Symmetry Pochette. Upper East Siders have no shortage of pretty handbags, and this specific silhouette is a hallmark in their rotation.
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Cream-coloured handbags with gold hardware always look luxurious.
An aptly named bag for toting around New York. It’ll hold all your essentials whilst shopping.
I’ve been eyeing this bag for about two years now. The mint green colour is refreshing and the shape is divine.
This bag feels very much like an accessory an Upper East Side tastemaker would take around the city and out to the Hamptons.
3. Structured Blazers
Style Notes: A blazer will forever be a staple in any capsule wardrobe, but if you ask someone from the Upper East Side, this specific garment should be structured and elegant. That doesn’t mean boring, not by any stretch of the imagination. Exaggerated shoulders, cropped lengths, structured sleeves—these are all unique details you can scope out when you’re shopping for a blazer that’ll remain with you for years but still feel interesting. It’s the first thing I’d consider reaching for when you want to make any outfit look polished, so it’s worth taking your time to find one you adore.
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The short sleeves and puffy shoulders make this a one-of-a-kind piece.
The sleek sheen and waisted silhouette of this jacket are so eye-catching.
Belts always add a nice touch, and I love that this is in a trendy tomato red hue.
This may have less structure, but the silky texture makes up for it. It’s the perfect option for lounging around on a Sunday morning in a luxe UES apartment (or at least pretending that you are).
4. Tailored Trousers
Style Notes: Like a blazer and a good pair of heels, every UES fashion insider has an exceptional pair of tailored trousers in their wardrobe. They’ll never lead you astray, always providing a sophisticated finish to any outfit, even when worn with a T-shirt. One of the best ways to make the most of its well-crafted silhouette and perfect pleats is by wearing it with a crisp button-down shirt, a sleek leather belt and the luxury-looking undone handbag trend. Together, you’ll have a look that fully exudes the Upper East Side sensibility.
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Linen will keep you cool in the summer and the darts will ensure you look elevated wherever you wear these to.
The Mason pant is a long-standing editor and fashion person favourite.
The wide-leg is easygoing, but the pleats down the centre still make this trousers feel polished.
The wrapped fabric makes these trousers look designer.
5. Stacked Jewellery
Style Notes: You’ll see plenty of Cartier Juste Un Clou bracelets and Tiffany & Co. Bone cuffs stacked on wrists and necklines around the Upper East Side. But aside from the brands, to me, it’s more about how the fashion tastemakers of the neighbourhood wear their jewellery. Rather than a single piece, they’ll wear stacks of bangles and bracelets or layer a T-bar necklace with a chunky chain. Rings also receive the stacking treatment, leaving you with a finish that’s truly the definition of “adorned.”
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Wear with a thin bangle or another chain stacked on top.
Soft, wavy shapes always feel particularly pretty.
Pair this chunky chain with a more delicate necklace.
This cuff is an eternal classic that’s always worth dreaming about.
6. Straight-Cut Denim
Style Notes: Of course, New Yorkers are on the pulse of trends, but any Upper East Sider knows the power of classic denim silhouettes. Case in point? Straight-leg jeans. As various trouser styles come in and out of fashion, the long-standing straight-cut will never disappear. It looks great with a nice top or blazer and layered under jumpers and coats come winter. In dark indigo shades or light hues of cream, this style of denim only makes your outfits look even more luxe.
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Wear these with a baby tee, an off-the-shoulder top or a boho blouse.
If you like the added volume of a barrel-leg jean, these are a great happy medium between straight-leg and more voluminous balloon styles.
One of the best straight-leg silhouettes I’ve seen in a very chic dark indigo.
A medium-wash blue is ideal for your everyday pair of jeans.
7. Dalmatian Print
Style Notes: New Yorkers, and Upper East Siders in particular, seemingly always know the print trends long before others—and how to use them in a way that’s sophisticated. If you’re a fan of patterns, from the check fashion trend to polka dots, you’ll certainly want to experiment with Dalmatian, which is one of the many chic animal print trends of 2026. It’s subtler than cow print, but still a stand-out with its minimal black-and-white colours and soft spots. Wear it as a handbag, shoes or a coat if you’d like to fully embrace an UES-approved statement.
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A fun clutch that both maximalists and minimalists can get on board with.
Shoes are a great way to try out a new print without committing to a bolder expression like a coat.
The print trend is even available in the form of jeans.
Another cute bag to try with a built-in top handle.
