Carlo Allegri/Reuters

Once he took my picture, it was easier to visualize myself fitting in.

My now-husband and I were on our third date—five years ago this week—when Bill Cunningham took our photo. For nearly 40 years, Cunningham—who died on Saturday at the age of 87—pedaled around New York City on a bicycle, snapping photographs of people on the streets. I count myself lucky to have been among them, because seeing myself through his lens changed how I related to the city.

I met Cunningham at Midsummer Night Swing, a dance party that sprawled across the plaza at Lincoln Center. It was a sticky evening. Sweat beaded down the back of my legs; big-band tunes bounced off the theaters’ grand facades. My date, Jason, was performing at the event. He wore a jaunty red-and-white striped shirt and flare-legged, blue polyester pants, white buttons marching up his hipbones. I was not dressed like a sailor poised to break out into a nautical-themed musical-theater number. In a crowd of swing dancers, that made me underdressed. That night, I was acutely aware that I wasn’t wearing the right thing, which would have been more in the vein of apple-red lipstick, pin curls, and shorts that nipped in at my waist. I hadn’t felt especially at ease in the plaza—but I also felt out of place in the city in general.

When I moved to New York in the summer of 2010, I was painfully lonely. I spent most evenings curled up next to a box fan, watching episodes of Lost. At the time, I didn’t even notice the pathetic poetry of it all. But like those ill-fated plane passengers, I also was stuck on an island that felt frighteningly unfamiliar, even if I had intended to land there.

My body was uncomfortable. I hunched in the crowds, slouching to evade jostling shopping bags and errant elbows. Bile lurched up the back of my throat when the train heaved itself across bridges. I felt my inner monologue shrink and shrivel in the face of so many people who were louder and more insistent.

Me and Jason, fourth from bottom right, in July 2011. (Jessica Hester/CityLab)

But by the following summer—when it was just too hot to stay in my apartment—I ventured out to try to find my tribe. And I did find them, in bookstores, museums, dance classes, nature walks—and, in Jason’s case, on OKCupid and then a hole-in-the-wall Polish restaurant where we ate sauerkraut and talked about all of the above.

And that’s how I ended up swing dancing in a green tank top and black skirt, skittering around the fountains, when Cunningham—wearing his trademark blue smock despite the heat—asked me and Jason to write our names down in his notebook.

In Bill Cunningham New York, a quirky and fawning documentary about his life behind the lens, Vogue editor Anna Wintour says, “We all get dressed for Bill.” But Cunningham didn’t photograph only subjects who looked straight off the runway. Many—maybe most—of his photos surreptitiously captured people who weren’t preening for the camera: elderly ladies trying to ford slushy puddles in ankle-length fur coats; shrimpy dogs with blue mohawks; a woman cycling past skyscrapers in a polka-dot dress, a tulle slip billowing behind her.

He sometimes depicted screaming patterns, searing colors, and outrageous makeup, but also less ostentatious tableaux: The thousands of characters who populate the sidewalks, making their way through the city every day, trying on identities and refashioning themselves.

In a reflection in The New York Times, Vanessa Friedman wrote:

His subject was not what was manufactured to catch his eye, but what people wore to feel part of the group, or to stand out from the group, or to otherwise telegraph their place in the world.

That’s what his photograph did for me. Seeing myself collaged next to so many other people from the same event made me feel proud that I’d shelved my anxiety and loneliness, at least for an evening, and thrown myself into the activities bursting at every corner of the city. Suddenly, it was easier to visualize myself here.

I wasn’t enamored with the outfit I’m wearing in the photograph—I’ve since given it away. But I’ve held on to the leaf of newsprint. I tucked it between the pages of a heavy book, and carted it from one apartment to the next. I stuffed it in a shoebox, where it cradled ticket stubs and pressed flowers. And a few weeks ago, just before my anniversary with Jason, I framed it. It’s an artifact from our early dates, when we were trying to track points of connection. But it also reminds me of my own affair with the city, and the moment I decided that I could make a life here—when I realized that, among these buildings and sidewalks, maybe I wasn’t as lost as I thought I was.

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