A new chapter in the history of New York street photography

When he was growing up in Queens, Johnny Cirillo’s mom thought he would one day become a talk show host. He loves chatting with strangers so much. “He would say to me: ‘You have so many questions. I couldn’t let someone pass without asking them a question,” he says with a laugh.

Instead, though, Cirillo, 44, ended up channeling his interpersonal curiosity into a quieter medium: Since 2016, he’s been known on Instagram and across the web as the photographer behind Watching New York, a street-style feed which shares daily photos of stylish city dwellers out and about on foot. In a way, he says, “it’s the natural progression of things.”

People will always care about the clothes of passers-by

Watching New York, who has 1.3 million followers on Instagram, has become known for his distinctive style, which consists of vertical shots with the subject perfectly centered, walking straight towards the camera with the background out of focus. Cirillo politely declines to share his gear and setup, and rightly so – he knows not to give away the secret sauce ingredients.

Now, after eight years as one of the city’s leading street fashion watchers, Cirillo’s first book of collected photographs hits bookstore shelves.

“Watching New York: Street Style A to Z” captures some of Cirillo’s favorite trends: K, for example, is for embroidery, C is for glasses—M is for patches, patterns, and so on. for prints, checks, colors and puffy sleeves. Although pictures speak louder than words, the book “Watching New York” not only honors the long tradition of street-style photography in New York, but also shows what has changed in it in the age of Instagram – and how street- style photographers are becoming household names in an increasingly crowded field.

Watch a video of Johnny Cirillo in action

His role model is Bill Cunningham

Cirillo’s book acknowledges in its introduction that it only exists because Bill Cunningham so memorably popularized street fashion photography in the late 20th century. When he died in 2016, “I felt a void,” Cirillo writes. “I thought that going out and doing what he did so well and devoted so much of his life to would be my way of honoring him.”

Thus began Watching New York, as a sort of homage to Cunningham’s work. Cirillo never expected it to last this long or become as well known as it has. The foreword is written by Gigi Hadid.

Looking at Cunningham’s work, “you can spot decades. You can identify certain eras, certain political movements,” says Cirillo. “He had his finger on the pulse the whole time.” Cirillo aims to maintain that tradition—in fact, he has previously provided expert fashion and trend analysis to the Washington Post, including insights into styles that have come and gone with the pandemic.

It honors the long tradition of street-style photography in New York, but also shows what has changed about it in the age of Instagram – and how street-style photographers are becoming household names in an increasingly crowded field

He has his own style

Of course, there are some key differences between Cirillo’s and Cunningham’s work: Cunningham famously liked to photograph people from the side, while the vast majority of Cirillo’s subjects are straight on.

Some of Cirillo’s subjects look directly into his lens, posing to the extent that one can do so while walking – giving the images a sense of interaction rather than observation. (Yes, sometimes he ends up running past people when he thinks he hasn’t gotten the shot yet: “I’ll catch up to them a block and try to do it again,” as many times as necessary, he says. And yes, he confirms with a laugh, that’s enough fast).

Cunningham sometimes took and published photographs of people who had no idea they were photographic subjects. When Cirillo began regularly posting his own photos, he did the same – until, as he writes in the book, “I posted a photo of a guy and a girl holding hands and smiling. Shortly after posting I received a message. That’s me in the photo. My girlfriend and I are huge fans of your work – unfortunately, that’s not my girlfriend in the photo.” Since then, Cirillo has asked each person he photographs for permission to post.

Mutual inspiration

After she captures an image, “we always talk afterwards,” she says – about Instagram permission, but also about the provenance of particular pieces and personal style philosophies. Many are making their own clothes – one young woman describes living with her grandmother during the pandemic as an inspiration to repurpose old clothes into a more modern, sexier look – “making dad’s clothes hot, basically”.

Post-shoot conversations are also how Cirillo met some of the recurring characters on “Watching New York.” A woman named Amber, whose clothes are featured in a two-page spread, says in the book that she likes “the ‘fire’ effect of personal style on other people – how an outfit can inspire a viewer to embody themselves in a fresh way ».

In the age of Instagram, Cirillo adds, getting subject permission is simply the most responsible thing to do. A photo that only appears in a print newspaper and never hits the internet “basically disappears after a few days”, while Instagram is “an archive”.

The big Instagram archive

“People go back years on Instagram and find people they know,” says Cirillo. “What if it’s two guys or two girls holding hands and the family doesn’t know? Or maybe even someone shouldn’t be in New York, you know?’

Does Cirillo worry about missing out on an opportunity to share a unique or exciting shot by leaving his subjects out? Not exactly: “98% of people immediately say yes to me. Two percent say no to me,” he says, “and usually half of that two percent I convince.”

As street photography has proliferated, both Instagram and sidewalks have filled up. Scott Schuman has over a million followers as The Sartorialist. Phil Oh shoots street fashion for Vogue and posts on Instagram as @mrstreetpeeper. Karya Schanilec provides real-time trend analysis as @karyastreetstyle. Brandon Stanton’s Humans of New York broadens the mission, depicting all walks of life in the city and the occasional striking outfit—Joshua Kamei’s @ladiesofmadisonave narrows its mission to (mostly) glamorous downtown women.

But Cirillo says street-style photographers rarely clash over material or territory. Some of his favorite streets and blocks – like some in SoHo – have been regularly patrolled by other street-style photographers for “years and years”, even before he started shooting there.

“We may be photographing the same subject, but it comes out completely different,” he says. For example, Cirillo loves running into Chaz Langley—whose work he describes as “intimate portraits of modern people”—and Jean Andre Antoine, who photographs each subject on expired Polaroid film. The latter “has his point where he stands every day,” says Cirillo.

“After a while, everyone finds a place where they feel comfortable,” he says, “and when you get there, it kind of feels like home.”

*With data from washingtonpost.com