Street Style Showdown: Upper East Side Vs. Williamsburg

Photographed by Jacqueline Harriet.
Last month, The Daily Beast published an article called "Why the Upper East Side Is Now Cooler Than Brooklyn," which argued that the land of lavish doorman buildings has become the latest retreat for hipsters looking to escape Brooklyn's rising property costs. While more affordable rents and a surge in trendy eateries and bars may be making the U.E.S. more appealing for 20-somethings hoping to plant roots in the city, we couldn't help but wonder if the stereotypical tweed-suits-and-pearl-earrings style the area is known for might be changing, too.
Obviously, we had to find out for ourselves. So, we hit the sidewalks of the Upper East Side and Williamsburg to see how the street style compares. What we discovered was an eclectic variety of some of the best-dressed people in New York City, with each neighborhood giving the other a run for its money. Click through for some serious outfit inspo and decide — which 'hood wears it best?
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Photographed by Jacqueline Harriet.
Name: Melena Lipman
Neighborhood: Upper East Side
Occupation: Student
What She's Wearing: Brandy Melville shirt, Topshop pants, Dr. Martens shoes, Alexander Wang bag, Ray-Ban sunglasses, and a Jennifer Fisher choker.
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Photographed by Jacqueline Harriet.
How would you describe style on the Upper East Side?
"It's very trendy and excessive, but elegant and classy at the same time."
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Photographed by Jacqueline Harriet.
Name: Sarah Saxty
Neighborhood: Upper East Side
Occupation: Co-founder of OVERT NYC
What She's Wearing: Nookie dress, Nike sneakers, Westward Leaning glasses, OVERT bag, and a Marc by Marc Jacobs watch.
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Photographed by Jacqueline Harriet.
Sarah sports a sleek leather backpack from her own collection.
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Photographed by Jacqueline Harriet.
How would you describe style on the Upper East Side?
"It's very woman-about-town, running here to there with uptown glamour."
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Photographed by Jacqueline Harriet.
Name: Gwendolyn Holder
Neighborhood: Upper East Side
Occupation: Assistant Manager, 077
What She's Wearing: Guess leather jacket, H&M T-shirt and pants, and Ray-Ban sunglasses.
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Photographed by Jacqueline Harriet.
How would you describe style on the Upper East Side?
"Very corporate."
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Photographed by Jacqueline Harriet.
Name: Kyra Angelakis
Neighborhood: Upper East Side
Occupation: Sales
What She's Wearing: COS dress, Roger Vivier shoes, and a Vito Nacci leopard coat.
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Photographed by Jacqueline Harriet.
How would you describe style on the Upper East Side?
"It's more structured fabric, structured suits. There's more of an old-fashioned, formal feeling."
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Photographed by Jacqueline Harriet.
Name: Katherine Keogh
Neighborhood: Upper East Side
Occupation: Gallery Assistant
What She's Wearing: Banana Republic sweater, Stuart Weitzman flats, Ray-Ban sunglasses, and a Paloma Picasso bag.
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Photographed by Jacqueline Harriet.
Name: Samantha Ho
Neighborhood: Upper East Side
Occupation: Public Relations
What She's Wearing: alice + olivia leggings, Theory top, Christian Louboutin boots, Chanel necklace, Céline bag, and jewelry from Cartier, Stella & Dot, and Hermès.
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Photographed by Jacqueline Harriet.
How would you describe style on the Upper East Side?
"Classy yet chic."
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Photographed by Jacqueline Harriet.
Name: Kalli Slater
Neighborhood: Upper East Side
Occupation: Student
What She's Wearing: Frame Denim jeans, Aerie T-shirt, Vince jacket, Givenchy boots, Chanel bag, rag & bone hat, and Dior sunglasses.
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Photographed by Jacqueline Harriet.
How would you describe style on the Upper East Side?
"It's very stylish, and ranges from all-black everything to really preppy."
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Photographed by Jacqueline Harriet.
Name: Sibylla Phipps
Neighborhood: Upper East Side
Occupation: Gymnast
What She's Wearing: Whistles trousers and Vagabond shoes.
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Photographed by Jacqueline Harriet.
How would you describe style on the Upper East Side?
"Rich and clean."
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Photographed by Jacqueline Harriet.
Name: Yeva Don
Neighborhood: Upper East Side
Occupation: Feng Shui Interior Designer
What She's Wearing: Louis Vuitton bag, Chloé shoes, and Thierry Lasry sunglasses.
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Photographed by Jacqueline Harriet.
How would you describe style on the Upper East Side?
"High style."
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Photographed by Jacqueline Harriet.
Name: Felicia Tsiokos
Neighborhood: Williamsburg
Occupation: Office Manager
What She's Wearing: American Apparel T-shirt, Black Denim pants, Jeffrey Campbell shoes, Verameat necklace, and Persol sunglasses.
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Photographed by Jacqueline Harriet.
How would you describe style in Williamsburg?
"Trendy, urban, and modern."
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Photographed by Jacqueline Harriet.
Name: Phoebe Marks
Neighborhood: Williamsburg
Occupation: Merchant, Madewell
What She's Wearing: Lefties jacket, Frye boots, Biltmore for Madewell hat, and a Kate Spade Saturday bag.
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Photographed by Jacqueline Harriet.
How would you describe style in Williamsburg?
"Eclectic."
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Photographed by Jacqueline Harriet.
Name: Nina Ragovski
Neighborhood: Williamsburg
Occupation: Events Coordinator
What She's Wearing: Boom Boom pants and Zara shoes.
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Photographed by Jacqueline Harriet.
How would you describe style in Williamsburg?
"There is no quote to describe it... it's open and not caring."
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Photographed by Jacqueline Harriet.
Name: Jenna Dombrowski
Neighborhood: Williamsburg
Occupation: Merchandising Information Coordinator, J.Crew
What She's Wearing: Madewell sweater, Zara jacket, All Saints pants, vintage APC Bag, Vagabond shoes, CRAP sunglasses.
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Photographed by Jacqueline Harriet.
How would you describe style in Williamsburg?
"It's almost like an identity crisis. Everybody is dressed so differently, everybody stands apart."
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Photographed by Jacqueline Harriet.
Name: Coco Layne
Neighborhood: Williamsburg
Occupation: Designer and Fashion & Apparel Student
What She's Wearing: American Apparel pants and a Bailey 44 top.
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Photographed by Jacqueline Harriet.
How would you describe style in Williamsburg?
"Williamsburg style is... *cough* *cough*."
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Photographed by Jacqueline Harriet.
Name: Tayler Smith
Neighborhood: Williamsburg
Occupation: Photographer
What She's Wearing: Dr. Martens shoes, Target purse, and SEE Eyewear sunglasses.
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Photographed by Jacqueline Harriet.
How would you describe style in Williamsburg?
"LOL."
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Photographed by Jacqueline Harriet.
Name: Jacki Huntington
Neighborhood: Williamsburg
Occupation: Freelance Filmmaker
What She's Wearing: Vince Camuto top, Coclico shoes, and Sock Dreams socks.
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Photographed by Jacqueline Harriet.
How would you describe style in Williamsburg?
"A friend of mine said once that Brooklyn is full of peacocks, and I don't think that's more true than in Williamsburg."
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Photographed by Jacqueline Harriet.
Name: Sally Tran
Neighborhood: Williamsburg
Occupation: Filmmaker

How would you describe style in Williamsburg?
"Relaxed and considered, but could be better."
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Photographed by Jacqueline Harriet.
Name: Shibon Kennedy
Neighborhood: Williamsburg
Occupation: Fashion Editor
What She's Wearing: Urban Outfitters dress, Best Friend jacket, Nicholas Kirkwood shoes, Illestva glasses, Loeffler Randall bag, and jewelry from AESA and Pamela Love.
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Photographed by Jacqueline Harriet.
An up-close and personal look at Shibon's leather Loeffler Randall bag.
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Photographed by Jacqueline Harriet.
Name: Jenni Crain
Neighborhood: Williamsburg
Occupation: Artist
What She's Wearing: Dana Lee jacket, Moscot sunglasses, and Anne Klein shoes.
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Photographed by Jacqueline Harriet.
How would you describe style in Williamsburg?
"Whatever anybody wants!"
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