How To Dress Like a (Real) New Yorker

New Yorkers set their own trends when it comes to street style
New Yorkers set their own trends when it comes to street style | © REX/Shutterstock
Photo of Jill Di Donato
Fashion Editor23 October 2018
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From all black everything to the party girl’s glitter go-go boots, there are some New York style stereotypes that ring true. Whether you’re a brand-new New Yorker or just visiting, here’s your guide to dressing like a New Yorker.

From New York Fashion Week to Anna Wintour and avant-garde designers, New York’s status as one of the most fashionable cities in the world has long been cemented. Now all you need to do is dress the part. With a dose of truth and a hint of irony, New Yorkers manage to lean into sartorial stereotypes while maintaining individual flair. Whether you’re donning dapper duds to get past the velvet ropes at a nightclub or just trying to navigate the subways without looking like a tourist, we’ve gathered the iconic New York styles to inspire your city look. You’ll look so good, people will stop you on the street to ask for directions.

Each New York neighborhood has a nuanced spin on style | © Jena Cumbo / Culture Trip

It’s true that New Yorkers have a penchant for black – it’s the uniform for fashion stylists, editors and photographers who want to be inconspicuous on set as well as a majority of the thousands of people you’ll pass by on the streets daily. But New York dressing is about standing out in a crowd as much as it is about blending in – how else do you connect in a city of 8 million? To help you harness this exciting sartorial tension, we broke down city-inspired styles by New York neighborhoods, with wardrobe advice on how to capture the style secrets of the Big Apple.

Chelsea gallerina

A look that captures Chelsea style | © Jena Cumbo / Culture Trip

Chelsea’s mash-up of priceless art and downtown cool gives the neighborhood a conscious cosmopolitan vibe. When people aren’t awestruck by a Kiki Smith painting, all eyes are on the sartorial gatekeepers of the neighborhood: gallerinas. The look combines savvy business dressing with lavish accent pieces. Think a black pencil skirt and silk blouse paired with a leather motorcycle jacket; gold bangles accessorize the look.

The hero: Black stiletto pump

Favorite New York designer: Alexander Wang

Shops at: Comme des Garçons

Upper East Side prep

A look that captures Upper East Side style | © ANDREW MORALES/REX/Shutterstock

For uptown girls, Queen B will always refer to Blair Waldorf, the fictional Upper East Side princess of Gossip Girl. With a nostalgic embrace of the classics, like pearl earrings and cardigan sweater sets, this look combines prep-school dressing with high-society elegance. Slip on an impeccably tailored varsity sweater, collared shirt, light-wash jeans and ballet flats.

The hero: Hermès scarf

Favorite New York designer: Cinq à Sept

Shops at: Bergdorf Goodman

Bushwick boho

A look that captures Bushwick style | © Jena Cumbo / Culture Trip

Bushwick, once an artists’ enclave and now one of Brooklyn’s more expensive, hip neighborhoods, is an epicenter for New York’s hipsters. Boasting exclusive nightlife, artisanal coffee and innovators in music and fashion, Bushwick knows how to cultivate a vibe. The look is an androgynous update on urban bohemian. To cop the Bushwick look, explore gender-fluid tunics, unexpected color-blocking and loads of accessories. Tailoring is unfinished, like a satin bomber jacket with asymmetrical sleeves. Anything DIY or repurposed scores a win here.

The hero: Denim crop top

Favorite New York designer: Chromat

Shops at: Urban Jungle

SoHo swank

A look that captures SoHo style | © Jena Cumbo / Culture Trip

The quintessential SoHo style walks the line between posh and punk, street and haute, but most of all is obsessed with trends. Think a Chanel tweed jacket paired with skinny jeans, suede mules and a Supreme bum bag.

The hero: Off-white handbag

Favorite New York designer: Marc Jacobs

Shops at: Rachel Comey

Debonair in Dumbo

A look that captures Dumbo style | © Jena Cumbo / Culture Trip

Dumbo, a riverfront neighborhood that used to be known for artist’s lofts and tech start-ups, has undergone a major renovation and is now home to pricey apartments, fine dining and a couple of members-only social clubs. The old mixes with the new so much that, when it comes to style, anything goes in this neighborhood. The look combines athleisure with the latest from emerging designers to communicate effortless chic. Achieve the look with boyfriend jeans paired with vintage cashmere and Balenciaga trainers.

The hero: Trench coat

Favorite New York designer: Luar

Shops at: Brooklyn Flea

FiDi’s new power dressing

A look that captures FiDi style | © Jena Cumbo / Culture Trip

The women of Wall Street work hard and play harder, and the result is a new wave of power dressing that takes no prisoners. This look is all about owning your style, whether that’s a pair of killer heels paired with a crisp blazer or animal print paired with Gucci slides. Stylish business casual that’s not afraid to go big with one statement piece delivers the look flawlessly.

The hero: Pantsuit

Favorite New York designer: Diane von Furstenberg

Shops at: Century 21

Village vanguard

A look that captures West Village style | © REX/Shutterstock

What do a hippie, a yuppie and a rock star have in common? The Village. Home to 18th-century townhouses, gourmet frozen yogurt and legendary jazz clubs, the Village epitomizes a downtown lifestyle that embraces joie de vivre. The look is cozy, urbane, eclectic. Try an embroidered maxidress, chunky cardigan paired with clogs and distressed denim jacket and Lucite jewelry.

The hero: Caftan

Favorite New York designer: Ulla Johnson

Shops at: Acne Studios

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