Meet The Street Photographer Who Chronicles New York City’s Evolving Style

From the depths of the pandemic sweatpants craze to the heat of hot vax summer, @watchingnewyork is watching you.

When photographer Johnny Cirillo headed out to photograph people on the street one day in 2016, he couldn’t have imagined that this photo project, @watchingnewyork, would turn into the biggest street style feed of the 2020s. On his Instagram and TikTok, he shares candid portraits of regular people going about their daily lives taken from a distance — but always with style and always with their permission. To scroll through his account is to feel a hit of inspiration — equal parts aspirational style and real-life envy — that makes me want to dust off all the wild clothes my mom saved from the ’80s and try them out in the real world. His work documenting New York’s most intrepid and stylish people inspires us to be bolder, take risks, and experiment with what we're wearing. It’s an unbeatable finger-on-the-pulse of an ever-evolving fashion moment. We spoke with him in September, just as he was gearing up to cover his first Fashion Week.

Left, a man in a crop top and jeans carrying a plant; right, two women embrace as they walk down a street, one carrying a skateboard

How did you get into photography?

My mom, who is 100% an artist who doesn't identify as one. She got me into photography when I was in junior high school. She’s the kind of person who combs the beach for shells and makes windchimes and jewelry. She is really creative; an artist in that way of life where she does things artistically every day.

She had an old 35mm camera that she let me play with and borrow. She taught me to print in black and white, and how to color with oils to bring the hues out in skin. In 10th grade, I had a great art teacher named Mr. Caskey, and he had a huge influence on me. I was really goofing off in school. He pulled me aside and said this is good, and he submitted my work to a magazine. I thought he was blowing smoke up my ass and just trying to get me to be a better student, but it got in. After high school, I started freelancing in New York — bands, weddings, engagement photos, and events like that. I was working in a restaurant during Hurricane Sandy, and when the restaurant was wiped out, I started freelancing full time. In 2016, I started street fashion, and it kind of spiraled.

Left, a group of four women in summer clothing, right a woman crossing the street in a green jumpsuit

Why street fashion?

I just loved the photos by Bill Cunningham that he did for the New York Times. The fashion was always secondary to the photography. I thought oh, that's a cool outfit, but it was the photo itself that I loved. I couldn't believe he got photos of people jumping over puddles on Fifth Avenue. When he passed away [in 2016], I thought I would go spend a day photographing like him just for fun, and to honor him. My wife, Kristin, saw the photos and encouraged me to keep working on the project.

I try to make a fun New York photo — blurring a cab out crossing a street, etc. Now it's like, that person looks really cool, how do I make it look good. The people added so much character to that photo.

Left, a woman with a pair of pants cut off around her neck. right, a man in a black skirt looking at his phone as he walks down the street
Left, two people in patterned clothes and black shoes cross the street, right, a woman in colorful primary colors and gucci clogs walks down the sidewalk

What are you looking for now, in 2021?

A lot of people got into altering their clothing in the pandemic, and so that's where my eye has been searching, for the one of a kind. The other day I ran into a woman with a pair of slacks cut off around her neck, she was like, "Me and my partner made this." I've gotten pretty good at spotting certain things. I'm out there so much. Some of [the outfits] are more detailed, so it could be focused, and I'll try to take a picture first and then assess the situation.

How did you settle on your photographic style?

I thought, if this project catches any momentum, I didn't want people to say, Well, he copied it exactly from Bill [Cunningham]. Which I did, I'm not taking credit for inventing anything new here, I'm just honoring him and doing it in my own way if that's possible. I decided to use a long lens because I love the candidness and naturalness of it; I didn't want people to see me. I wanted to see people from 100 feet away and then approach them afterwards and ask them if they minded if I shared the image after I explained the project.

This year is the first year I'm going to photograph outside Fashion Week. Not because I've been wanting to do it — the surprise of capturing people on the street who aren’t expecting it is my favorite. I love the idea of people not knowing and being like, Oh, wow. Thanks. You noticed it.

Everything up to now has been natural. Shooting Fashion Week isn’t going to change my Instagram, I'm still going to be shooting in the street every day. I want to keep the aesthetic and for it to grow organically instead of being forced into photographing the most outrageous Fashion Week portrait, that's not what it's about. It's candid, it's natural, it's relatable — real New York moments.

Left, a couple walk down a crowded street, right, a man and a woman in a fancy dress walk down the street

Did the pandemic affect how you work?

People dress either how they feel, or as a way to express themselves. During the pandemic it affected my work — I stopped freelancing, I stopped doing weddings and started working more on my personal projects. The pandemic definitely changed how people dressed. The masks came out, the T-shirts and the bandanas and homemade masks, then surgical masks and then all the big companies started making masks. When people had their faces covered up, they were dressing a lot more risky, kind of a secret identity thing. Now, everything is really bright and vibrant and happy; I think that people are really excited to be outside. There was a darkness to what people were wearing at the beginning of the pandemic — leisurewear, comfortable clothes, big layers. Now it's more open, colorful, bright, mesh, handmade, fun.

Are a lot of the people you take pictures of influencers, or real people?

No, they're not [influencers]. But I do notice that a lot of them are very creative people. Authors, hairdressers, tattoo artists. Other people are working people who just have great style, in my opinion.

My favorite photos are when I secretly catch my wife and my son walking around, but that's a personal thing. My other favorite shots are happy couples. I'm a sucker for it. I love when they're looking at each other. I also have a folder called coordinating outfits, where you can tell that duos or people are wearing similar outfits, and they're matching. I'm generally trying to surprise people. I do follow up and ask permission from every single person that I photograph and post online. And if they say no, then I don’t share it. Some of the best pictures are the ones that people have never seen. I get told no all the time.

Left, an older woman in a mask and hat leans on a cane, right, a man dressed in cowboy gear talks on the phone as he walks down the street

What would you like to change about the project moving forward?

Inclusivity. I don't have a problem covering everybody, because it's New York, there's so much diversity, which is great. But what I get the most shit for is body diversity, people say that I don't post enough heavyset people. I get wrecked when someone says in the comments, "Another day, another skinny person. This guy never shoots heavyset people." I'm really trying to do that. Women with head coverings are another one. A lot of people are happy to be photographed but say, "Please don't post the pictures."

There's a balance, and I would love people to be in my shoes for a day and see what I see. I want to make sure that the people are stylish, and also I'm trying to appease, and as the account has grown and gotten bigger, the demand is more now. Every time you post, you don't know who you're going to offend. Everybody gets upset about everything. It's tough when you get bigger, that there's a microscope all the time. I don't want to hurt anybody.

Left, a woman in a handpainted jumpsuit, right, two men hold hands as they walk down the street

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