There are times you catch yourself wearing your Downtown outfit Uptown and feeling just slightly out of place. Sure, it’s New York, you can wear whatever you want, and no one’s really watching. But still, there’s that moment you text a friend “what are you wearing?” before dinner at The Monkey Bar or while picking out a birthday gift at Tiffany’s. And the same thing happens before a night Downtown. Dinner at Ha’s Snack Bar and  after  drinks at Smuck, different vibe, same ritual. Because in this city, it’s not about following rules; it’s about reading the room.

Uptown

This is old-school New York, the version you picture when you think of the city: Breakfast at Tiffany’s, the Ralph Lauren Mansion, and Blair Waldorf in a headband. 

Image of Carolyne Bessette Kennedy & JFK Jr.

Uptown style leans polished and “elegant,” but that doesn’t mean it’s uptight. After all, Carrie Bradshaw lived on the Upper East Side, proof that Uptown dressing can be playful, bold, and far from traditional. It’s 2025, and the definition of “classic” has evolved.

Image of SJP as Carrie Bradshaw in Sex and the City

Still, if you’re meeting friends for martinis at The Carlyle, you’ll probably lean into something a little more refined, the kind of outfit that says you could meet your boyfriend’s parents after and still look perfectly put together. 

Downtown

If Uptown is polish, Downtown is instinct. This is the New York that smells like espresso and vintage leather, the kind of style that looks accidental, but never is.

Image of Charli XCX

Think Kikis, The Bowery Hotel, and a closet that mixes designer with something you found at a flea market. It’s less about what you wear and more about how you wear it 

Image of Zoe Kravitz

Downtown style is fluid, a little chaotic and completely unbothered. You don’t plan the outfit; the outfit finds you somewhere between the West Village and the Lower East Side

And if you’re still not sure what to wear, you can’t go wrong with all black, it’s timeless, effortless, and very New York. This isn’t a bible or a rulebook; it’s New York. Style here has never been about following rules.

Text by: Wika Soto-Hay