What Your Dog’s Outfit Says About You

Johnny Cirillo is famous for his work chronicling the outfits of New York City’s most stylish citizens on his street-style Instagram account, @watchingnewyork, but more and more, lately, he’s been turning his attention to their equally stylish dogs. With absolutely adorable results. 

Cirillo took his first street style photo in June of 2016. Bill Cunningham, the grandfather of modern street style photography, had just died and Cirillo wanted to pay homage to the iconic chronicler of New York City style. “I really liked his work and I thought it would be a nice thing to do for the day,” he says, chatting on the phone from his home on Long Island where he lives with his wife, Kristin, their young son, Cassius, and a 17-year-old American Pointer named Louisiana. “I didn’t know him. I never spoke to him or even saw him in person. But when someone passes […] sometimes you just want to put yourself in their shoes, and I guess I was trying to put myself in Bill’s shoes.”

Cirillo launched “Watching New York” in July, the following year. “[At first] it was just a personal side project I was doing for fun — I have a lot of those — but it just kept drawing my attention and became a passion,” he says. Seven years on, and he’s got nearly a million followers and street style has become his primary professional focus. 

He haunts a handful of street corners in three high-style New York City neighborhoods — Williamsburg, SoHo, and Union Square — for the majority of his pics. A tall, somewhat eccentrically dressed, 40-something with a full beard and a big-ass camera, he’s easy to spot and says he is approached five to 10 times a day by fans of his work. “It’s wild,” he says. “But I appreciate it so much when someone comes up to me and wants to chat or tells me something nice. Not about myself, but when they say someone I photographed encouraged them to step outside their comfort zone [with their own look], that’s a great honor.” 

He’s so recognizable at this point that people often dress up just for him, in the hopes of making it onto his account. “I know they do it because they’ve told me,” he says. “Sometimes I’ll see somebody walk by me three or four times with an outfit that’s not exactly what I was looking for that day. Then I’ll get a message that night saying, ‘Hey, I walked by you today. Was my outfit not good enough?’ But some days I just want to do trends. Like, I’ll decide I’m only photographing bucket hats. And, of course, if something stupendous comes along, I’ll shoot it, but otherwise I just block everything else out.”

And, should a beautiful, well-dressed dog cross his path, well, that’s always worth pressing the shutter button for.

Are people usually pretty open to you photographing their dogs?

Usually. I tend to shoot people (or their dogs) while they are still pretty far away and then, as they approach, I let them know who I am and what I’ve done and make sure they are OK with it. I think it’s only happened one time that I didn’t get the shot, and I asked the person if I could shoot their dog again and they said, “No.”

What makes a really great dog outfit?

Well, they’re always adorable, but I have seen some luxury dog outfits that — I’m not saying they’re necessarily better, but they’re different and I like them. I saw a dog wearing Fendi one time. 

Logo Fendi?

Yeah, logo Fendi.

So, not “stealth luxury,” then.

No. 

There’s been a lot of talk in fashion media recently about the rise of “stealth luxury” — from the more understated aesthetic of the most recent runway shows, to Gwyneth Paltrow’s ski-trial outfits, to the costumes on the latest season of Succession. Is this something you’ve noticed on the streets as well?

Not so much. What is rising is maximalism. I used to get one good maximalist shot a month, and now I get a few a day. I haven’t really noticed the stealth thing yet. But, then, I’m not often shooting in locations like Tribeca or the Upper West Side, where that could maybe be happening.

And I suppose not noticing it is sort of the point. Also, looking at your feed, it does seem like you are more drawn to maximalism, in general.

I like minimalism, too. When either of them is done well, you sort of can’t take your eyes off of them. But I guess what I am drawn to about maximalism is the fanfare of it all — the excitement, the loudness. It’s fun. And it’s very approachable for me. It says something about your personality: I’m big, I’m fun, I’d like to talk. You know? Minimalists sometimes give off the vibe that they’re maybe not as approachable.

Does the same thing go for their dogs?

I think owners are always going to dress their dogs like they dress themselves, but I’ve definitely been seeing a lot more dog outfits recently. Five or six years ago, I didn’t see nearly as many as I do now. I think it’s kind of a flex on your outfit to have your dog dressed in something similar. But I definitely see dog-dressing on the rise. 

What does the way a person dresses their dog tell you about them? 

When you dress your dog — even just putting booties on to make sure their paws are safe on the streets of the city — it lets me know that you are going that extra mile, that you are really treating your pet like your best friend. I’m not saying dog owners that don’t do that don’t care, but I’m pretty sure that the person who is doing it cares a lot. That’s the vibe.

Do you dress your own dog up?

Oh, yeah! She’s got a bunch of outfits. My favorite is probably her shark outfit. It’s got a fin on the back, and it’s got a hood that you can pull over her head, and it turns her into a little shark. She wears that quite a lot. And she’s got this great little brown sweater for when it’s cold out. She has, like, three or four little sweaters.

Personally, I love seeing a dog in a hoodie or something with a faux-fur collar. That always cracks me up. Or when they have little sleeves, like, it’s a proper sweater, instead of just something that covers their back. Or I love a full jumpsuit. An outfit from head-to-tail. That’s always really adorable to me. 

Are there any dog-fashion brands you particularly like?

I have no idea, but I probably should. You know what I would love to see, though? Second-hand shops selling old dog clothes. I feel like that would do really great — just like a little rack of outfits for dogs and cats. I’ve heard rumblings that it could be happening soon. Honestly, thrifting seems to be bigger than ever right now. And I don’t know if you would call this a trend exactly, but homemade clothes have become more and more of a daily conversation that I’m having with people. It’s unbelievable.

So many times when I say, “Boy, I’ve never seen that before. Where did you get it?” They say, “I made it myself, yesterday.” So I think that that’s a very big trend right now — people learning how to sew and how to take something apart and put it back together the way they want. It’s definitely on the rise.

Tell me more about your dog!

Her name is Louisiana. She’s 17.  I got her in my 20s, and now I’m in my 40s. She’s amazing. I guess she was the runt of the litter. We have a house out on Long Island, and she runs all over the property, chasing squirrels. We’ve been through a lot together. 

How did you find her?

I had just been through a breakup, and I was feeling a little down in the dumps. I visited theNorth Shore Animal League in Fort Washington and got her from there when she was about five months old. She was a Brooklyn dog for the first 15 years of her life, but then we got the place on Long Island, so now she’s enjoying her twilight years out here.

What’s she like?

She’s very tough on strangers. It takes her a long time for her to let her guard down. My little brother Nicky and I are basically the only people she wants to jump up on and stuff. Nicky actually took her for the first 100 days of the pandemic, so they quarantined together and are really tight. She’s really smart, too. She does every trick in the book. At one point, I even trained her to buzz me into my apartment. 

And she loves camping. We go upstate a lot. She loves the water. She can dive! If I put an “x” on a rock and throw it into the water, she’ll dive down and pick it up and bring it back to me. Even at 17, she’s still very sporty. She’s pretty independent, though. She doesn’t need a ton of attention, and she lets you know what she wants. She goes by the front door and will bark if she wants to go out and plays footsie with her dog bowl if she’s hungry. 

Does she like getting dressed up?

She doesn’t mind the sweaters, but if it’s a loose one she’ll squirm her way out of it, and she hates wearing booties on her paws. 

It doesn’t sound like you dress her in anything too wild, though. What’s the most ludicrous thing you’ve ever seen a dog wearing?

Once, at a Mets game, I saw a dog walking around with a pipe in his mouth. It was almost like a bone, but it was a pipe. And then he also had on sunglasses and a Met’s hat. It was pretty unique. I’ve got the photos somewhere.