Johnny Cirillo is Watching New York

By Brian Braiker

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New York, Johnny Cirillo is watching you. Literally. Since 2016 Cirillo has stationed himself on street corners in Williamsburg and Greenpoint, where he’s lived for over 20 years, and snapped thousands of photos of fabulously attired New Yorkers.

It started as an homage to the late great Bill Cunningham, the New York Times street style photographer, but the passion project has very much morphed into its own thing: On Instagram, where he has nearly one million followers at Watching New York, and more recently on TikTok, Cirillo posts candid shots of — and interviews with — stylish Brooklynites.

It all adds up to a sizzling slice of life in the borough, all swag and panache. And over the years it’s gone from the hobby of an obsessive to a full time job for Cirillo. Look out for the Watching New York coffee table book next year.

Johnny Cirillo is this week’s guest on “Brooklyn Magazine: The Podcast.” Here, we discuss Watching New York, how it came to be, where it’s going and some interesting encounters he’s had along the way.

This interview has been edited for concision and clarity. You can listen to it in its entirety in the player above or wherever you get your podcasts.

You’ve got a nice mustache. I like the thick mustache and the light beard around it. It’s a good look.
Yeah, my wife doesn’t love it so much, but thank you. I appreciate it. I’m going to tell her that you said that.

You’ve shot for us and I’ve been incredibly grateful because the stuff you’ve been doing is great. It’s a series that I think you came up with a name for, Looklyn. How did we meet? Did you reach out to me?
I did. To be honest, it was early. It was early days. It was before Watching New York really got as big as it is now at least. And you were nice enough to give me the opportunity to jump on board. Anything printed to me is special. Anything Brooklyn related to me is special, and I like that feeling of community. And I worked a lot with Greenpointers, and I always enjoyed doing it. So I was thankful when you responded and we started chatting and had some ideas together, and I think it was an amalgam of your ideas and my ideas that got us there, but I’ve enjoyed doing it very much.

Shout out to Greenpointers. I check in on them at least once or twice a week, and I think our readers should too. How do you describe what you do at parties, if you meet someone for the first time? It’s not just “I’m a photographer.” What is it?
I have to tell different people different things. You have to know your audience. If you’re telling somebody that’s a little bit older, like when I’m talking to my parents’ friends, they might not know what it all means. Basically, I say “I consider myself a photographer before a fashion guy.” Fashion came second. I never knew one single thing about fashion, not a thing. I knew that I really enjoyed the pictures of Bill Cunningham. I enjoyed his dedication to the streets and what he did year in and year out until he was in his 80s. And I respected that enough to where, when he passed, I thought that it would be just an interesting way to either put myself in his shoes, to feel what he was feeling or to honor him for the day.

I enjoyed it so much. And when I went home, it was a fun project for my wife and I to talk about because she’s really into fashion. So she started teaching me about, “Oh, that’s this and that’s this.” So basically now I think they’ve mixed and I know an okay amount about fashion, I think I’d like to know. I still just shooting what I think looks cool.

Bill Cunningham was, for those who may not know, a legendary photographer. New York Times. He would camp out in Midtown and shoot people crossing the street. He lived in Carnegie Hall. There’s a really good documentary about him and his process. What was it about him, that not being a fashion person yourself, that drew you to him?
A couple things. One, I’m attracted to personalities. I like open-minded kind, personalities. I’ve seen a couple interviews with him over the years and I thought he was a fascinating person just to listen speak. Photography can be a slog when you’re out there and you’re shooting all day, it gets tiring. Especially I was doing weddings and events and stuff like that, and I was doing them for years. And you do start to get tired of it. You have to dig deep sometimes to go back out there and do another wedding.

So when I started noticing that he’s been doing this for 40 years, whatever it was, I said, “Man, the way that he just goes out there day in and day out is so impressive to me.” Then I started looking more into his work and his photos. I started following along more and just appreciating his commitment, his daily commitment. It was his way of breathing to me it seemed, and I really respected that.

When did Watching New York start to become its own thing?
I did a podcast that was called Profiles:NYC. And this podcast was just me and this guy Austin, and this was the introduction to doing Watching New York to me. We did this for about a year. We would walk around the city and interview strangers and he would do the interviewing. He would interview them for 10 or 15 minutes, and then I would do the portraits of them at the end. That ended in June of 2016, and then also in June of 2016 is when Bill Cunningham passed away. It was a good timing for when the podcast ended, he got picked up by Gimlet. So it was good timing. So it started off as just I would go out a few days a week. I wasn’t posting about them, I was just enjoying the process and learning. I was using a lens that I never used before, and I was enjoying that.

After about maybe four months, it started to become a little bit more of an obsession of when the weather was a certain way I couldn’t miss this anymore. And I started rearranging my schedule. If I had things scheduled, headshot, portraits and maternity shoot, whatever it may be, if something happened on that day, the weather, if it snowed, if if was raining, I started rescheduling things and it started to become more than just this project. And I started feeling more like I wanted to document more and I wanted to archive more, and I was really enjoying. Then I started saying, “Let me get through the year. Let me do one full year and then I’ll have this nice thing that I can look at and be proud of.” I still wasn’t sharing it. I wasn’t sharing any of the images.

Oh, really? I didn’t realize that, okay.
And then after the year, there was just no turning back, I think. It just became something that I love like fishing or checkers, chess, whatever your hobby is. Something that you like that you don’t get tired of. Video games, whatever it is. It became one of those things that I just really enjoyed, and then I started putting them up on Instagram.

What is the process like today? You’re out on the streets, you tend to stay close to home in Greenpoint, right? Maybe Williamsburg. I know you shoot with a super long lens and you see them coming down the boulevard from a distance. What are you out there doing?
It’s a relaxing experience for the most part. I put on my music. I have a 5-year-old kid, I have a wife at home, and life is busy as far as him with school, activities, friends, picking him up. So this is my therapy in a lot of ways. Not that I want to be away from them, but it’s good to have your own time. It’s good to be alone in doing the things that you like to do. I put music on, I stand on a corner that has a good intersection, four different ways. Usually like Bedford Avenue in North Fifth Street where Awoke Vintage is, and the pizzeria, the subway’s a block or two away.

And I really just look as far down as I can. That’s my goal, to look 1.5 blocks away in all directions. And when I see something that I think looks interesting, I try to square my shoulders up with them and get right even with them as they’re coming down. And I have to wait for the right opportunity for nobody to be in the way. I use a 200 millimeter, so they’re usually about, I don’t know, maybe 70 to 80 feet away from me when I photograph them.

And they have no idea you’re down the block taking pictures.
These are candids. I try to catch as much as I can, candid New Yorkers not ready for me. That’s the vibe. Somebody called me a few years ago, the people’s paparazzi. That’s the idea behind it. I’m paparazzi for you, for me, for people that are just walking around. I do my best to get the shot. And then when they get to me, I stop them and I ask them if you would mind if I shared your image on social media? And I explain to them, and then that’s it. That’s the process. Then I go home and I edit and all that.

You make it sound simple, but what’s the ratio of pictures that you take in a day to pictures that end up on your social media account, that people actually see?
A good day is a thousand photos. Anything under 400, 500 is a slow day for me. But out of those 1000 pictures, I will take 20 pictures of a person. I’ll rip off 20 shots, but I will take a thousand pictures in a day. And out of those 1000 pictures, maybe I captured 40 looks. Now out of those 40 looks, I whittle that down. When I sit down with my wife, I’ll whittle that down to probably 10. And out of those 10, I bet you I only use two. Probably two a day I get. Between two and five a day after everything is all said and done.

All right. So you see someone coming down there, incredible look, you take it, you fire off 40 pictures or whatever, and then they get closer. At a certain point, they either notice you or like you say you go up to them. What is the success rate of them being cool with it?
I have been grabbed before by the back of the neck, by the shirt being yanked.

Is that a one-off or is that happened more than once?
It’s happened maybe three times. I’ve been grabbed once, physically grabbed once.

Was it Sean Penn?
No, it wasn’t. I have been flipped off by a celebrity, which is funny because I don’t technically shoot celebrities. But then I caught up with him and I spoke with him. When a celebrity sees somebody with a big camera, they just immediately assume it’s paparazzi, it’s going to go in these paparazzi magazines or whatever. And I guess he got angry with me and flipped me off. But it’s okay.

Who is the celebrity, can I ask?
Should I say it? Yeah, sure. I can say it, I said it before. It was Rami Malek. And I think he had just won the award for best actor. And I love him. I appreciate him. But I picked up my camera and he immediately turned his back. He was with his girl, and he gave me the finger for the duration of his walk down Bedford Avenue. And then he turned down north Sixth Street. And I said, “I’m going to go the other way and try to cut him off and explain” because I felt bad.

Did you realize who he was at that point?
Of course. I didn’t, at first. When I first saw him, I was only photographing his girlfriend. I think it was his girlfriend. She had this beautiful outfit on. I didn’t notice him until he flipped me off. I said, “What the fuck did that guy flip me off for? Then I was like, “Oh, wait a minute, that’s Rami Malek.” And then I went around the block and I caught up with him and I explained to him, “Hey, look, I’m sorry, I saw you flip me off. I’m not paparazzi. I shoot street fashion in New York.” He was okay. He was cool about it. It’s probably a hassle getting you photo taken all the time.

So. You’ve been grabbed.
Oh, well, yeah. I have been grabbed a couple times. And people do get mad, so that’s another reason why I like to use the long lens. I don’t get right up in someone’s face with a 35 millimeter and hit them with it. The success rate for younger adults under 30 is very high. I would say it’s 95 percent. Older people, I would say over 60, it’s a 10 percent success rate, and nobody wants to share their picture.

Interesting. Is that product of growing up on social media you think?
I don’t know what it is. Or some of them, especially when I find much older people, let’s say in their 80s, they don’t understand it. They’re like, “What are you doing with…” I say, “It’s for social media. It goes on the internet.” And [they reply] “I don’t want to be on the internet.” All right, all right. But for the younger generation, it’s a pretty high success rate. Lately, which is interesting, which hasn’t been great. When people recognize me, they actually will then tell me, “Wait a minute, I know who you are. This isn’t my best outfit. I don’t want you to use that picture.” So I’ll lose some like that, which is a bummer.

I was just going to ask that. At what point does the observer get observed, and how does that alter the phenomena of street fashion?
I’ve been observed and there’s been some really nice articles written about me, which is cool. The only people that really recognize me are people that are really into street fashion or heavy into photography. So I’m not getting recognized all the time. But I do get recognized if I’m holding my camera and I’m walking around the city or Brooklyn. People will stop me and chat and stuff, which is really nice. It’s nice to be recognized for something that you worked hard on.

Of course. I imagine some people are like, “Hey, shoot me.” And you’re like, “Nah, you’re wearing, like, Levi’s.”
Without saying that, I see somebody walk by me three or four times. And then sometimes I’ll get a message at night that says, “Hey, I was wearing this today. I walked by you a few times. Can you tell me how come you didn’t take my picture and stuff?” I feel terrible.

Oh, that’s rough.
And I tell them this, there are some days that I concentrate solely on something and I block out the rest. So if I’m looking for, I don’t know, overalls, I really hunt for the day, overalls. I want to make an overall album this week. That’s all I’m going to do. And if I concentrate hard enough on it, I can probably find them. Sometimes I have tunnel vision and I don’t really notice everybody that’s walking by me. So that’s usually what I tell them. Hopefully they understand.

When did it become a thing monetarily, or is it a thing monetarily? Do you consider this your day job now, or do you do corporate gigs to pay the bills? How does that work?
This is it. This is full-time now, which is really great. Yeah, I got very lucky. I’m very happy about that. I don’t take it for granted. I’m happy to be here where I’m at. One day, about two years ago, I got a message from Pandora, the jewelry company, and they asked me how much would it be for them to put a necklace on somebody in one of the photos. I had never done a sponsored post or anything like that, so I was like, “How much do you want to pay me?” And then they told me how much they wanted to pay me, and I was like, “Yeah, sure, I’ll do that. I can skip work this week.”

And then I was like, “Maybe I should get an agent.” So then I found an agent and I talked to them, and then I’ve been with the same agency now for a couple of years, and they find me the work. I pass on a lot though, honestly, I really try to stick to things that are on-brand and things that I believe in and that I really like. I’ll do it if I like the product and stuff like that. I won’t push it if I don’t.

That’s interesting. So with the Pandora example, you’re putting one of their pieces of jewelry on someone that you would’ve shot anyway, or did you find the model? Because I would imagine the whole point of Watching New York is you’re capturing people who are organically themselves. If you go and put a product on them, it’s less organic. Was there any tension there for you?
There was for sure. There’s something that you feel morally wrong about doing that. I worked with Gucci this year. They gave me a couple products. So what I said was, “I’ll do the ad if you let me choose people that I’ve already photographed in the street, and if you let them style it the way that they want.” And they said okay. So they got to take a piece, it was a hat and a sweater or whatever, and style it exactly the way that they wanted. And then I would say, “Hey, I’m going to be over here. Cruise by me.” So in a way, yes, that is staged. They do know that I’m there. I am going to take their photo, but I did let them style it themselves, and I try to keep it natural that way. That’s the best I can do.

What makes your subjects so compelling is not the brands that they’re wearing, it’s what they do with the articles of clothing. Some of them make it themselves, some of them just tweak it It’s not the thing that they select off the shelf, it’s the way they style it that makes it special.
I just want to say that I never take money from small New York creatives that are making things. People call me out all the time, like, “Oh, you’re supposed to say that this is an ad” when it’s not an ad. I love meeting New Yorkers that have their own businesses, that are making their own garments and clothing and hats or whatever. So I try to find them when I can and put them on a pedestal if I can, to just let people see who’s out there. You don’t have to always buy from the big brands, but there’s smaller companies out there that are working really hard, family owned businesses that are worth looking into.

Yeah, you shout them out, you use your platform. And then at a certain point, you picked up TikTok. How was moving to TikTok? You still do the street style photography with your camera, but then you’re adding another layer on that. Was there a learning curve for you, and how’s it going?
TikTok is infuriating. I cannot figure TikTok out. Instagram is very consistent. I know what I’m going to get when I post, my interaction. TikTok goes from one extreme to the next, and I cannot figure it out for the life of me. I’ll try things out there. I’ll see if they work. Sometimes they go nowhere. Sometimes they work, whatever it is. But my cousin, who’s 24 or 25, was ushering me to try TikTok because… And this was about two years ago, so she said, “You should do some interviews, you should make some interviews with people and post them.” So I started doing that and it was very good. It got very big very quickly, and then it just flattened out. Where Instagram has always been just this climb, which is nice because it’s my livelihood now. I have a family and stuff, so it’s important to me. TikTok is more just like, let’s throw something at the wall and see what sticks to me.

I think we’re roughly the same age, I think I’m a little older than you and I love Instagram, but we’re Brooklyn Magazine, we’re going to try getting on TikTok this year. That’s one of the goals. And see what we do.
What’s good about TikTok, to me, that’s different than Instagram is that you don’t have to have the pressure of this is my grid. It’s so important. If something fails. TikTok to me is almost for failures. You can try it if you want, and if it doesn’t go anywhere, nobody even sees it and who cares. You don’t get judged on it. Instagram, to me, is a little bit more stuffy in the way that people judge you on a post that doesn’t do well. A little more freedom on TikTok, I think.

Yeah, same. I do worry about the “how do you do, fellow kids” vibe. We’ll cross that bridge when we get there. When did you pick up a camera? Where did this start?
I was 14 in the ’90s. My mom was into photography back in the day, so she showed me some of her photographs and stuff, and she would show me these black and white photos, and she would print them on matte paper. She still had these oils that she would color the cheeks a little red and give them some color in their face and stuff. I just thought it was fun. And she had an old camera that she gave me, and I took it to school. And I started enjoying the process of just photographing friends and documenting what was going on in the hallways of school and stuff. And that was the beginning of it. And then I didn’t take it seriously though, until 11th grade. I had this really nice teacher, Mr. Caskey. I loved Mr. Caskey. I was a total hassle. Anybody would say it. I was a total hassle in school. I just wasn’t a great student.

Class clown?
I guess, oh yeah, not bad in the sense I didn’t get into a ton of trouble, but mischievous. Yeah, class clown and just a pain in the ass. Just trying to be loud and funny. I was a kid. And Mr. Caskey, when I was in 11th grade, I took photography as a “Yeah, I like photography. It’s fun. I can goof off. I don’t have to go to class if I don’t want. No one’s going to get mad. My parents aren’t going to care what I do.” So I took some photos and he didn’t coddle me or anything like that. He was tough. He was a tough guy, but in his way, in his teaching ways, very kind. But he took one of my photos and said, “I think you should enter this into high school contest.” I don’t remember if it was statewide or the country or whatever, but I blew him off.

He ended up putting it in there for me, and it made it into this magazine. Didn’t win the prize, but it was recognized as, “Hey, here’s a cool photo that somebody took from this high school out on Long Island.”

And you weren’t annoyed with him to take that liberty?
No, I thought it was cool. I thought it was really cool. It was one of the first times I remember thinking like “He thinks I have some kind of potential.” I saw that he cared. And the next day I remember going into class and being like, “I’m going to buckle down a little bit more.” And then I started cutting my other classes to go to photography. And then I got obsessed with the dark room. Until I graduated high school, I lived in that photography lab and I did everything.

And then I talked to him about building my own dark room. He talked to me about the chemicals that I needed to get and everything like that. And after high school, I built my own dark room and continued. And then I moved to Brooklyn in 2003, I think, and just kept on shooting and taking pictures of bands and stuff like that. And then I had a job in a restaurant for a very long time because I needed to pay the bills. And then around 2010 is when I started full-time freelancing. And 2016 I started Watching New York.

You moved to Brooklyn in 2003, but you’re what, you’re Jackson Heights born and raised in Long Island?
I lived in Queens until elementary school. I was born in Jackson Heights, and then we moved to Middle Village, and then we moved out to Long Island basically for school. And then after a couple of years after high school, actually, I went to a local college over here, and then I moved to Brooklyn in 2003.

Nice. And Greenpoint, the whole time? Lot of changes. A lot of changes in 20 years.
Yeah. Wow, you ain’t kidding, man. West Street. West Street’s the biggest change of it all. West Street, when I moved there, I swear… First of all, nobody went over. There was nothing there. Not a thing. Not one single thing. All bombed out cars on the street that looked like they were burned and left for dead. There were dogs, wild dogs that lived in the streets down there at that time. You never went down there. Nobody parked their car there. It was a ghost town. And now you go down there and it’s all built up.

And it’s hipster central and gentrified.
Funny. Hipster didn’t used to be the word that it means now. In 2003, hipster was cool. It was like, “Oh, he’s a hipster.” It’s like, “Ah, cool, man. All right.” Now when you say that, everybody says it, it’s derogatory.

That’s funny. I landed in Brooklyn the year before you did, and I’ve been in the Park Slope area the whole time, and talk about lot of changes. It was already on the, obviously more gentrified side of things, but it’s just gotten crazy. The prices are insane. If I were to move here now, I couldn’t afford it.
No way. No chance. I was struggling back in the day and the rent was cheap, real cheap. I remember one of my friends at one point got an apartment. It was big. It was a studio on Franklin Street, and it was a thousand bucks. And I remember thinking, “How the hell are you affording this?” I had other friends that had studios for 500 bucks that I was like, “Cool. All right. That’s basically where my rent was, 600 bucks or something like that.” This thousand dollars that he was paying I thought was out of control. That place could be $9,000 now. It was huge.

I’ve heard you talk about anxiety in the past. What interested me about you saying that you have anxiety is that you put yourself in a situation that, for me would be the most anxiety-triggering I can imagine, which is walking up to a stranger. Just asking strangers questions and taking pictures of strangers strikes me as nerve-wracking. How does your anxiety manifest? Or was that never an issue in that scenario?
Anxiety’s different for everybody. And it’s funny because when you tell somebody about your anxiety, they don’t understand, “Oh, how can that give you anxiety? Who cares? I don’t feel that way.” And I feel that way too when someone tells me, “Oh, I get so much anxiety. I would never be able to walk up to a stranger and talk to them.” Doesn’t bother me at all. I enjoy talking to people. I’m prepared for them to blow me off and I could brush it off my shoulders. It doesn’t bother me.

When I started going to therapy, I was told, and it makes a lot of sense, that I have something called anticipatory anxiety, which is when you are approaching something or waiting for something or the unknown and letting that build in your mind and fester into the worst case scenario. So when I would have a wedding to shoot and I’d be the sole photographer, the closer I would get to that day, it would just build and build and build. “What if I get the flu? What if I break my leg? What if something happens and I can’t be there and I’m going to let these people down?” I hated the pressure of feeling like I had to be somewhere at a certain time. Even my own wedding, the morning of my own wedding, an hour before my wedding, I went to a river with my fishing pole and I walked up to my chest and I just went fishing and I left my phone behind because I was panicking about approaching this moment.

Weddings are scary when they’re yours.
It is, it was, yeah. Okay, so I’ve never been on an airplane before. I’ve never left New York before, still.

Right. I’ve heard you say that. So, still?
Yeah, I’m working on it. But the thought of working up to getting on a plane, I’ll make myself sick. If you told me “In three days from now, we’re going to get on a plane and take this flight,” but I’d be so nervous I wouldn’t be able to do it. I’d get knots in my stomach. But if you were here right now, if you were knocking on my door and I open up my front door and you said, “Look, dude, there’s a plane right here. You want to get in it?” I can go in it like that.

So it’s not fear of flying. I totally understand anticipatory anxiety, because I think I have probably a milder version of it. But anytime I have a big event the next day, even if it’s something I’m excited about, the Five Boro Bike Ride, which I try to do every year. I can’t sleep the night before. My stomach’s in knots. And it’s a thing I enjoy and it makes no sense to me. I’m like, “Why am I all twisted up about this thing that I’m excited about?”
But then when you’re there, how do you feel when you’re doing it? Right? Same like my wedding. As soon as it kicked off, I was like, “Oh, good. I’m here. I’m doing it. I’m loving it.” But it’s that anticipation that gets me sometimes.

All right, I’m going to show up on your doorstep with a plane ticket to somewhere cheap be, but we’re going. Grab a bag, we’re going to fucking Cincinnati tonight.
I have a friend that actually has his own plane. He does his own private flights. He goes out to Montauk once a week. He goes to Manhattan. He’s like, “It’s a small plane.” He said, “But if you want to try it, come with me and I’ll take you out to Montauk.” Takes him 20 minutes to get out.

Yeah, Montauk is short. Yeah, there you go.
So I might give it a shot, to see what it’s all about. But I got to get out there because my kid’s 5 now.

Your kid’s 5? He’s going to want to travel, right?
Totally. Yeah.

When you and I have talked in the past, when we talk about your schedule or what you’re able to do or where you’re able to shoot, I think I’ve tried to be like, “Can you try other neighborhoods?” You’re pretty rooted to your home base and your childcare schedule and your family. Fatherhood’s a major part of your identity. Has it changed you in any fundamental way or has it just rooted you more? How has that affected your life?
It’s the greatest thing in my life, and everything revolves around my wife and my kid. And really him and getting him what he needs and having memories with him and playing with him and doing that. I see myself now, when he was born, I never thought of my parents in a certain way until he came along. Now I realize what they’ve done for me, how they’ve tried. I didn’t think about those things before, especially when they’re very little and you’re getting up in the middle of the night constantly. You walking at two o’clock, three o’clock in the morning, back and forth, trying to get them to fall asleep, trying to get them to eat a bottle, trying to get them to calm down. And then you realize, “Oh, my mom did this for me. My dad did this for me. I got to call them in the morning, and I never thanked them for… I’m tired.”

So I really enjoy experiencing things with him. I take him with me sometimes to take pictures. We went out the other day together and took pictures together and he gets into it. I got him his own camera. Mostly I do whatever he wants. He likes playing with dinosaurs and stuff like that. And I get on my hands and knees and crawl around and pretending I’m a dinosaur and do whatever. It’s been the greatest joy of my life. Nothing else comes close to meaning anything to me or mattering than it does him and Kristen and just being with the family.

Same. That’s great. Strong dad vibes, we like that. That’s good. We should start a dad’s club. Mine are a little older, but it doesn’t end. Last night, my 14-year-old, she was not feeling well. It was a long, rough night. And it’s like, “Come on, we’re still doing this?” We’re still doing it.
Yeah, for sure. I don’t think it ever really stops. My mom and dad, they come over here and I have a problem with something and they take care of me, or they give me advice or “You need anything?” Or whatever. So probably I can’t never see it really ending. I talk to my dad every day, once a day about all kinds of things. But a lot of things with, “Hey, I was thinking about doing something with the grass over here. What do you think?” He’s a wealth of knowledge. He’s been through it. And my mom too. She loves talking to me about Watching New York and stuff. We’re all best pals still, which is great. And hopefully, fingers crossed, that’s the way Cash and I will be, and Kristen growing up, hopefully.

Does gear matter to you, or is it… There’s the saying that it’s a bad carpenter who blames his tools, but does gear make a difference?
I would love to know these creators that say gear doesn’t matter. I can’t figure it out. I like good gear. I need good gear. I need my camera to be very fast, very sharp. I need it to perform under extreme conditions, when it’s raining, when it’s snowing. So I do think that it matters in a way. I could definitely do what I’m doing to an extent with a 20-year-old digital camera, if I had to, but it would not afford me the liberties that I have with my camera, which can shoot 24 frames a second if I needed to. Those are important. I’m trying to catch every little step. I’m trying to get the right step in the right moment.

Things like a fast shutter speed are important to me. I like things that are tack sharp. New Yorkers especially, are in a rush. If they’re walking fast. So having something superfast is helpful. The cameras that I try to use, they focus and take the picture the same exact moment. Yeah, to me it matters.

The quality of the gear. Or do you care about the brands? You just care about the gear itself?
No, I don’t care about the brands. I’m a Cannon guy, but that’s only because I’ve had all their lenses for so many years now. I’ve been looking more into Sony and stuff like that. But I’m so invested that it’s hard to make the change. But if somebody like Sony wanted to say, “Hey, you want to try a couple of these?” I’d say, “Yeah, sure.”

Current fashion trends. Is there anything you’re noticing? We’re here, we’re mid-March, it’s third winter, it’s early spring, whatever you want to call it. What are you seeing these days that’s newer, interesting?
People making their own stuff, which I really love. Taking garments and altering them in some way, cutting a piece out and adding plaid to that, or adding pockets or turning it inside out and undoing it in certain places. Letting the frays hang down. I’ve been noticing a ton of people making their own clothes, which is really fun and exciting. I’ve seen some really beautiful stuff.

Has it affected how you dress at all, this project?
I’m sure. Yeah, I guess it has. There’s like a guy that I photograph all the time. One of my favorites, Darnell, he’s a very fashionable dude.

He was in one of the issues of Brooklyn Magazine, wasn’t he?
I think he was in the first, actually. Yeah. I met him I think that day that I did that issue on him. It was about two years ago or something like that. I’ll call him up and say, “Hey, dude, I need some gear. Can you come with me?” And we’ll go thrifting together and we’ll spend a bunch of money on a ton of outfits for that season. I’ll put things on it. And then he’ll say, “No, no, let’s try this. Let’s take this off. Let’s put this on.” So he helps me out a lot. And then Kristen, my wife knows a lot and she gets me a lot of stuff. I think I’m okay. I don’t know.

No, you’re stylish. You’re definitely stylish. When we do launch our TikTok, we should do “Thrifting with Darnell” as a series.
Yeah, really should for sure. I’ve thought about it. We’ve talked about that as an idea for a segment, and I just haven’t done it. It’s so funny because during the day, if I have my free time, it’s so hard for me to spend it not on the street taking pictures. I always feel like I’m missing something, even when I’m doing something else for Watching New York. Even when I’m shooting for brands, I can’t turn it off. If I see something coming, I just got to do it.

I was going to ask what a typical day in Brooklyn is when you’re not shooting and it sounds like you’re shooting.
I always take my camera with me. If we’re going to go out to lunch, if we’re going to hang out or go to the park, I usually will find somebody when I’m out just walking around and take a picture. You never turn it off, but not complaining about it. I enjoy it very much.

Do you have advice for young photographers who see you and you found your lane, which is amazing. It’s hard to find your lane. What would you advise them?
Two things. One, it’s so funny that people always say, “Do the things that you love. Just keep on doing what you love and people will eventually recognize it and see it, and you’ll get a group of people that appreciate your work and they’ll start following along,” or whatever. I never thought that that would ever happen. I always would hear people say that and say, “No, that’s stupid.” But I did what I did and I did it for a pretty long time before anybody really noticed it. Probably not until 2020 or 2021 that people start really noticing it.

So that’s like four years in?
But you have to have a passion for it. I tried a lot of things: “Oh, this can go viral. Oh, this could be cool.” My heart wasn’t in it. So Watching New York, shooting street fashion was something that I did, I would do. If Instagram went away, if TikTok went away, if all the internet went away, I would still do it for myself because it’s something that I enjoy. You just got to find what you like. It could be shooting pictures of lemons, who cares? It’s whatever it is. If it makes you happy, there’s going to be somebody else that relates to it out there. And you’ll find an audience for it, if that’s what you’re looking for. Mostly though, it’s important to just make yourself happy and do something that gives you purpose.

And then the other piece of advice that I think is really important is to surround yourself with people who believe in you and encourage you. Don’t talk to people that give you a backup plan. If you want to do something, talk to people that say, “Do this or die trying.” And that’s it. Go down with the ship as it’s burning in the middle of the ocean if you have to. But do what you love and surround yourself with people that pat you on the back, even for the smallest accomplishments.

I a hundred percent echo that, because it’s invaluable that people believe in you. Because when you don’t, you feel it.
I know. I still doubt myself. I really do. You read articles and stuff, and sometimes I come across something. I came across this stupid article, a post on Reddit the other day about me, I was on Reddit, just looking at Reddit, and I saw this thing about Watching New York, and I said, “I shouldn’t read this.” And I read it.

Never read the comments.
It messed with me a little bit, because sometimes when they pick apart the things that I question, “Am I doing this thing? I don’t know, maybe I could do better here.” And then strangers start talking about you saying, “Oh, oh man, maybe I was right about that, maybe.”

Can you give an example of what that is?
To be honest, I tried my best to block it out. It was a full therapy session talking about it with my therapist. Part of it was about my photography. Because I like to think that my photos are good. And people started picking apart the photos a little bit and saying like, “It’s dog shit. It’s this, it’s that.” And I started saying, “Is it not good?” “Oh, the colors are bad.” Someone said something about the color, my editing was not good and I had to just brush it off and just say, “That’s your opinion. Not everyone’s going to agree with me.”

Look, A) it’s all subjective. B) there’s a lot of jealousy out there that manifests in ugly ways. I think your photos are great.
Thank you, Brian. I appreciate that. Thanks a lot.

I’ll pat you on the back any day. You’re working on a book, you have something coming out in spring of next year. Are you allowed to talk about that? What is the project?
It’s going to be a street fashion coffee table book, Watching New York’s street fashion coffee table book that I’m super excited about. And I’m in the thicket of it right now with Abrams publishing company in New York. And I’m working with this great publisher and we’ve been talking every day. I’m in the middle of writing the intro right now. And we’re figuring out which pictures are going to go where and what’s going to be the tone of the book. And basically, yes, it’s going to be a street fashion book, but it’s about belonging and feeling like you belong, wherever you are. Your crowd is out there somewhere and you shouldn’t feel alone.

That’s one of the things that I really love about shooting street is that you find somebody that might look really different to you and people are scared by that. But then when you put them out there, I get a lot of messages saying, “Thank you so much for posting this. I felt like the only one.” To me, there is a thing, it’s about belonging and it’s about feeling accepted and seen. And I hope that translates.

You’re Watching New York, but your work travels beyond New York and people can dress literally however they want here and no one bats an eye. But that is not the case in other places.
I get that a lot. Especially some of small towns in the middle of the country. People say, “Oh, I would get killed if I wore something like this. And people would laugh at me if I wore something like this.” But the truth is probably if you did it, somebody else would probably see it and they’d probably say, “Oh, he’s doing it.” Or “She’s doing it, maybe I could do it. If they’re doing it…” And that’s how community is built, which is important. The reason why New York is so great is it’s a bunch of, you can call them weirdos if you want because they’re different, but that’s what makes it so great. It’s a huge melting pot of people’s expressions just dripping all over the place. So everywhere you go, there’s somebody that you can relate to.

Who’s the first photographer you remember admiring or the first photographer’s name you knew or book you bought? What’s the first big influence?
There was two. One of them was a David LaChapelle book that I can’t remember which one it was. The other book was CRAZYSEXYCOOL and it was by [Holly] George-Warren, and it was all these celebrities. It was portraits, but they were really, really interesting. I remember Tom Hanks has these werewolf hands that he’s putting on his face, and Drew Barrymore is in these boxing gloves and Patrick Swayze’s wearing a dress.

David LaChapelle is interesting because he’s so stylized and you’re like the opposite of that.
Yeah. I’ve always really loved really old black and white photography, I’ve always really loved. But the celebrity stuff, to me, especially when I was living out on Long Island, seemed so far away, so untouchable, especially in the ’90s. Now, it feels like celebrities, you’re more in touch with them. You hear more from their voice. I was a little kid in this town on Long Island, they felt like Gods. So seeing them acting silly or doing something fun and thinking about the photographer, putting them in those positions was always just really exciting to me to look at.

Do you still shoot film ever? Or is it entirely digital?
I do shoot film. I shoot quite a bit of film. I have a medium format camera. I have five 35 millimeter cameras. So I’ll take one of them out and if we’re going to a birthday party or something like that, and I’ll click off three or four shots and I’ll put that one back in my closet. It usually takes me about a year to get through all of the film, or a year and a half even to get through all of this five or six cameras that I have, different events. And then I bring all the roles and I love it. It’s a time capsule. You wait to get it developed. You see them, you didn’t see them when they happened. There’s no digital screens on them. I enjoy film very much.

I actually had an idea for an app if anybody’s out there and wants to do it. I thought it would be cool to have an app on your phone, a 35 millimeter app, where you take a picture. There’s a set amount of time, let’s say 30 days where you can’t see that picture for 30 days. In 30 days it’ll pop up and it’ll be like, “Hey, your film is ready. It’s been developed.”

That’s cool. A friend of mine that I went to high school with bought a bunch of disposable cameras and mailed them to 10 people and said, “Take one or two pictures, put them in an envelope, mail them someone else. And then once the camera’s full, sent it back to me and I’ll develop them.”
Oh my God, that is such a cool idea.

I think I’m going to steal that idea. Or you can steal that idea.
Let’s do it together. Let’s do it for Brooklyn Magazine.

I actually love that. We’ll do it. Done. Project in the works.
Yes, dude, I love that. That sounds so fun.

Anything you want to want to shout out before we go?
I just interviewed these two brothers from the Bronx and they’re a really cool family-owned business called Lavi NYC. I ordered something off there. I got a silk scarf that I just got in the mail yesterday and I love it. Their dad was in fashion in Harlem back in the ’70s, I think they said. They’re making these beautiful pieces. They make starter jackets, they make these really beautiful starter jackets, these scarves. They make a lot of apparel and really cool stuff. So if I could shout somebody out, just because it’s one of the most recent, I really enjoy their company.

Check out this episode of “Brooklyn Magazine: The Podcast” for more. Subscribe and listen wherever you get your podcasts.