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When photographer Johnny Cirillo set out to photograph people on the streets one day in 2016, he couldn’t have imagined that this photo project, @watchingnewyork, would become the biggest street style feed of the 2020s. On his Instagram and TikTok , he shares candid portraits of ordinary people going about their daily lives from a distance – but always in style and always with their permission. Scrolling through her account is feeling a whiff of inspiration – equal parts ambitious style and real envy – that makes me want to dust off all the wild clothes my mom saved from the ’80s and try them on in the real world. His work on the most fearless and stylish people in New York City inspires us to be more daring, to take risks, and to experiment with what we wear. It’s an unbeatable on the pulse of an ever-changing fashion moment. We spoke to him in September, as he was preparing to cover his first Fashion Week.
How did you come to photography?
My mother, who is 100% an artist who does not identify as such. She introduced me to photography when I was in college. He’s the kind of person who scours the beach for seashells and makes chimes and jewelry. She is really creative; an artist in this 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 how to print in black and white and color with oils to bring out skin tones. In grade 10, I had a great art teacher named Mr. Caskey, and he had a huge influence on me. I was really fooling around at school. He took me aside and said it was good, and he submitted my work to a magazine. I thought he was blowing smoke in my ass and just trying to make me a better student, but it happened. After high school I started freelancing in New York – groups, weddings, engagement photos and events like that. I was working in a restaurant during Hurricane Sandy, and when the restaurant was destroyed, I started working as a full-time freelance. In 2016, I started street fashion, and it kind of skyrocketed.
Why street fashion?
I loved the photos of Bill Cunningham he did for the New York Times. Fashion has always been secondary to photography. I was thinking oh that’s a cool outfit, but it was the photo itself that I liked. I couldn’t believe he had pictures of people jumping over puddles on Fifth Avenue. When he passed away [in 2016], I thought I would spend a day photographing like him just for fun, and to pay tribute to him. My wife, Kristin, saw the photos and encouraged me to continue working on the project.
I’m trying to make a funny photo of New York – blur a cab crossing a street, etc. People have added so much character to this photo.
What are you looking for now, in 2021?
A lot of people took to changing their clothes during the pandemic, so that’s where my one-of-a-kind eye looked. The other day I ran into a woman with pants cut around her neck, she was like me and my partner did that. I got pretty good at spotting some things. I am so out there. A part of [the outfits] are more detailed, so that it can be focused, and I’ll try to take a photo first and then assess the situation.
How did you choose your photographic style?
I thought if this project got big, I didn’t want people to say, Well he copied it exactly from Bill [Cunningham]. What I did I don’t take credit for inventing anything new here, I just honor it and do it my way if possible. I decided to use a long lens because I like its candor and naturalness; I didn’t want people to see me. I wanted to see people 100 feet away and then approach them afterwards and ask them if they mind if I shared the picture after explaining the project.
This year is the first year that I will be photographing outside of Fashion Week. Not because I wanted to – the surprise of capturing unsuspecting people on the street is my favorite. I like the idea that people don’t know and be like, Oh wow. Thank you. You noticed it.
So far, everything has been natural. Filming Fashion Week isn’t going to change my Instagram, I’m still going to shoot in the streets every day. I want to keep the aesthetic and have her grow organically instead of having to shoot the most outrageous portrait of Fashion Week, that’s not what it’s about. It’s blunt, it’s natural, it’s relatable – real New York moments.
Has the pandemic affected the way you work?
People dress either as they feel or as a way of expressing themselves. During the pandemic, it affected my job – I quit freelancing, quit doing weddings, and started working more on my personal projects. The pandemic has definitely changed the way people dress. The masks came out, the T-shirts and the homemade bandanas and masks, then the surgical masks and then all the big companies started making masks. When people had their faces covered, they dressed in a much riskier way, a sort of secret identity. Now everything is really bright, vibrant and joyful; I think people are really excited to be outside. There was a darkness in what people wore at the start of the pandemic – casual clothes, comfortable clothes, large layers. Now it’s more open, colorful, bright, mesh, handmade, fun.
Are most of the people you photograph influencers or real people?
No they are not [influencers]. But I notice a lot of them are very creative people. Authors, hairdressers, tattoo artists. Other people are hardworking people who just have a good style in my opinion.
My favorite photos are the ones where I secretly catch my wife and son walking around, but that’s a personal thing. My other favorite shots are happy couples. I’m a fan of it. I like when they look at each other. I also have a folder called Coordinating Outfits, where you can tell that pairs or people are wearing similar outfits and they match. I usually try to surprise people. I follow up and ask permission from everyone I photograph and post online. And if they say no, then I don’t share it. Some of the best pictures are the ones people have never seen. I am told no all the time.
What would you like to change in the rest of the project?
Inclusiveness. I have no problem covering everyone, because it’s New York, there is so much diversity, it’s great. But what I piss off the most is body diversity, people say I don’t post enough big guys. I’m devastated when someone says in the comments, “Another day another skinny person. This guy never shoots big people.” I’m looking for body diversity, but sometimes it takes me a week to find a tall, beautiful person. I’m really trying to do this. Women with headgear is another. A lot of people are happy to be photographed but say, “Please don’t post the photos. “
There is a balance, and I would like people to sit in my shoes for a day and see what I see. I want to make sure people are stylish, and I also try to appease, and as the account gets bigger and bigger, the demand is higher now. Every time you post, you don’t know who you’re going to offend. Everyone gets upset about everything. It’s hard when you get fat, for there to be a microscope all the time. I don’t want to hurt anyone.
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