NYC’s Upper East Side is a Treasure Box of Street Style

Get ready to want to dress up.


So much of the street style that gets shared during New York Fashion Week happens downtown, especially now that the hubbub no longer hubs around Lincoln Center. But people in other areas of New York City wear clothes to marvel at, too — year-round, regardless of the official fashion calendar. And by all bagels that are hole-y, you deserve to see them!

In the first set of what is sure to be a wardrobe-inspiring sartorial exploration of NYC’s five boroughs and many neighborhoods, Simon Chetrit took the 6 train uptown to Manhattan’s Upper East Side — home to Museum Mile, Blair Waldorf, the part of Fifth Avenue that out of towners think of when you say “Fifth Avenue” and a whole lot of style.

We asked him to zoom in on those who have reached the age of wisdom, those with enough years under their well-worn belts to remember a time before sweatpants in public were considered more or less black-tie. (Athleisure and ripped jeans are key components of the downtown wardrobe.) And of course, he did just that. But he also captured old souls living in young bodies who were occasion-ready, too.

Click through and see for yourself.

Photos by Simon Chetrit.

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  • Angela Gentile

    When I grow up, I want to be the woman in picture 5.

    • me

      me too!

      think i’ll plagiarize her all-black look tonight : )

  • me

    Shout out to Simon: ” SIMON ! SIMON ! ”

    Love peeping newyorkers going about their bizness & looking fab : thx, bro.

  • Pork & Cookies

    LOL. Blah.
    I live by there.
    -Kirsten // pork & cookies

  • Natty

    OH HELL YES! I’ve been longing for MR to break out of its downtown coverage and explore the happenings uptown. Excellent photography; hope there is more where this came from!

  • So many chic people in NYC, it always amazes me. And the elderly at the ballet! Oh man are there some amazing styles!

  • Hellbetty666

    All of these outfits are TO DIE. the fella in the green suit can get it. So much wicked style.

  • Everybody looks so faaaabulous!!!!!

  • Moe

    Damn there is nothing cooler to me than an older man with style. I love how fly these older businessmen are!

  • elpug

    i just love joy radiating from the woman in the first image.

  • Greer Clarke

    Someone help me find the guy in the background of 6

  • The 3rd!

  • I love seeing the oldies dressing up so fabulously. Unfortunately in Australia, unless you are frequenting specific events or boutiques you never see older people dressed so well. The tweed coat in pic 1 is amazing and reminds me of Chanel’s current Spring/Summer campaign.

    Adrianna x

  • I absolutely love this! I can’t wait to see more!!!

    Laila from Townhouse Palette

  • Tess

    I’d like to think #6 is about to march into her office and ask for a deserved promotion.

  • Suzy Lawrence

    Men in well fitted suits! Swoon.