How Can I Avoid Looking Like a Tourist in New York?

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A better question may be what would make you not fit in? There are so many different versions of New York, so many layers of history and psycho-geographies — uptown and downtown; literary New York and financial New York; the hipster havens of Bushwick and Greenpoint — that almost anything goes, as long as it comes with the right attitude.

Indeed, the quintessential New York look may be more about how you carry yourself than how you actually dress. This is a city, after all, in almost constant flux, made of people largely from elsewhere, who, as Darren Walker, the president of the Ford Foundation once told me, come to New York to reinvent themselves or become more themselves; to leave their mark.

We were talking about the former fashion editor André Leon Talley, who in his operatic self-presentation, favoring sweeping caftans and towering hats, was one kind of quintessential New Yorker. When I asked colleagues to name some others, the answers included the writer and critic Fran Lebowitz (who favors men’s suits), the actor Chloë Sevigny (known for her eclectic wardrobe), the artist Patti Smith and the social doyenne Annette de la Renta.

They look very different, but the one thing they share is a clear sense of their own character, built from the inside out and expressed in the ways they dress. That’s what makes them seem so New York. Whatever you wear, said Raul Lopez, the founder of the Luar fashion label, wear it with aplomb. Worrying that you won’t fit in is the thing that makes you not fit in. (Well, he added, that and waiting patiently at the corner for a traffic light to change to green.)

That said, there are some styling hacks to keep in mind. Lauren Santo Domingo, the founder of the online retailer Moda Operandi and the recently named artistic director of Tiffany’s homewares, offered some strategic advice:

  • New Yorkers still dress for the theater. Tourists do not. So if you are going to Broadway and want to look like a local, dress up rather than down.

  • New Yorkers are generally focused on what is coming next. That means size up when it comes to knitwear, suiting and coats. Anything too slim or fitted (this includes skinny jeans) will mark you as not from here. Also, if you want to look really insider-y, she said, “throw your chunky oversize knit sweater over your coat instead of a scarf, and tuck your oversize tote under the arm, not on your shoulder.”

  • Finally, don’t be flashy. New Yorkers are into layered suiting, oversize totes, muted tones (black, white and grayish greens), undone hair and makeup.

As for that last one, in some ways it’s a reflection of how much the built environment of cities defines how we dress (or how much we dress to reflect our environments). New York is a metropolis of concrete and skyscrapers; a city turned inward, away from the water; a city built on a grid. There’s a toughness and a grit to the streets that is reflected in the colors and shapes of its clothes.

Which brings me to the last key aspect to avoiding looking like a tourist in New York: the walk. Whatever you are wearing, remember to stride fast, with purpose and direction. Even if you have no idea at all where you are going.

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.