The Photographer Documenting How New Yorkers Actually Dress

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Style Points is a weekly column about how fashion intersects with the wider world.

For years, street-style peacocks would be stationed outside runway shows as New York Fashion Week took over the city—and Johnny Cirillo was not there.Fashion week would be going on and I would just be on Bedford Avenue walking up and down,” his camera in tow, he recalls, because I liked the idea of [documenting] the regular 9 to 5 person coming and going to work and the grocery store.” He wanted to see people in what they actually wore, not what they wanted to be seen in,” he says. “Carrying a pizza box or walking their dog, but looking awesome.”

a couple of women walking down a sidewalk with shopping bags

Johnny Cirillo

One of the images in Johnny Cirillo’s new book Watching New York.

Nowadays, Cirillo does shoot some fashion week street style. But he’s best known for the more unfiltered looks he documents on his Instagram account, Watching New York (his followers now number 1.3 million.) Cirillo calls himself “the people’s paparazzi,” and he is one of a handful of photographers currently reimagining street style in a more quotidian direction. He captures the stylish essence of one of America’s few walkable cities; while the rest of the country has their cars, we have our coats, bags, and yes, pizza boxes.

a woman wearing red sunglasses, a blazer and cargo pants

Johnny Cirillo

Another Cirillo street style shot.

Today, some of his work will officially be between hardcovers. Watching New York: Street Style A to Z (Abrams) collects highlights from several years of street shooting, categorized alphabetically from Accessories to Zebra Print. The colorful volume was inspired by Bill Cunningham’s weekly street style dispatches (Cunningham has been a huge influence on him; the account began as a way to honor his work after his passing) And it even boasts a foreword penned by Watching New York follower Gigi Hadid. “I was looking for one line from her, you know what I mean?” Cirillo marvels. “Anything that you can give me.” Instead, she wrote a touching mini-essay about what his work means to her.

Johnny Cirillo Watching New York: Street Style A to Z

Watching New York: Street Style A to Z

Johnny Cirillo Watching New York: Street Style A to Z

The alphabetical approach showcases the survey-like nature of Cirillo’s oeuvre, which documents city life in the uncertain 2020s and celebrates the thrifted, bricolaged looks of passers-by. The account grew to include video, and a robust TikTok presence, after Cirillo realized there was more to the story. He would look at images by other photographers, he says, “and wonder, ‘What happened right before this? What happened right after this?’” Now, he often interviews his subjects about their personal stories.

a person in a cowboy hat and leather jacket walking down a sidewalk

Johnny Cirillo

A Western look from frequent Watching New York subject Darnell.

Watching New York watchers have since grown attached to some of the account’s recurring characters, like a young man named Darnell, who shared his story of growing up in foster care. “He had some dark times, but he came out the other side a better person. I got a lot of messages about that. So did he. And I still do, actually,” Cirillo tells me. Another subject people responded to was a designer named Monday Blues, who was wearing garments made from coffee bean bags and explained that they had previously been unhoused. As a necessity, they fashioned clothes from discarded Starbucks coffee bean bags. Later, that experience would inspire their fashion designs.

a group of women in bright clothing

Johnny Cirillo

A group of women on Galentine’s Day, photographed for Watching New York.

Conversations about fashion, Cirillo has found, can give way to something deeper. “You’d be surprised by the amount of people who will just open up to you when you approach them kindly and in a curious way: ‘Hey, you look really cool. Can you talk to me about what’s going on and what’s your story?’ All of a sudden you start getting to the real meat and potatoes, which is deep inside of all of us: sadness, being lonely, fighting through it, getting better, being stronger, having the bravery to continue.”

a couple of men smiling

Johnny Cirillo

The Bell brothers, photographed by Johnny Cirillo.

Until recently, Cirillo hadn’t been to many big cities besides his proving ground of New York. A fear of flying kept him from traveling widely, until recently his wife, he says lovingly, “gave me a kick in the ass. She surprised me with a flight and drove me to the airport.” Since then, he’s been to Paris twice.

So, what’s his review of the City of Light? “Paris is beautiful, the fashion is incredible, and the people are amazing, but it’s much more subtle and reserved. In New York, you never know what you’re going to get—or what somebody made out of a coffee bean bag.”

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