- Photographer Johnny Cirillo has been documenting New York's fashionistas since 2016.
- His account @watchingnewyork has 920,000 followers on Instagram, and nearly as many on TikTok.
On the same day legendary style photographer Bill Cunningham died in June 2016, another photographer picked up his camera and hit the streets of New York City.
Johnny Cirillo wanted to honor Cunningham by trying street style photography, but he already had plenty of experience behind the camera. He worked as a freelance photographer for events like weddings, engagements, and maternity shoots, making time for creative endeavors on the side.
Cirillo, now 42, told Insider that he didn't have an interest in capturing street fashion until he stepped into Cunningham's shoes.
"When I looked at his photos, I didn't always look at them because of the fashion. I liked what he was doing in the streets and how much he was hustling," he said.
For Cirillo, the appeal of fashion photography was its complexity. He wanted to photograph clothes the way people wanted them to be seen, which presented an interesting challenge in the city's busy sidewalks. He was hooked.
What started off as a small project became @watchingnewyork, an account where he chronicles NYC's most fashionable. The page has amassed more than 920,000 followers on Instagram and more than 886,000 followers on TikTok, where he shares interviews with his subjects.
Seven years into the undertaking, Cirillo shared his best tips for expressing yourself with clothes, exuding confidence, and finding the right lighting and angles for your best 'fit pics yet.
Go bold with your style — thrift stores are great for one-of-a-kind items that help your personal style flourish
Cirillo told Insider he's always on the lookout for "the bold, the unique, and the creative." He recommends finding an inspirational outfit photo and recreating it with pieces from your closet first.
For those who don't have what they need at home, the photographer said, "You can find everything at a thrift shop."
Although Cirillo knows more about photography than fashion, he said he's learned about style from his subjects, even thrifting with them on occasion. He noted that textures like faux fur and corduroy can pop onscreen.
The key to nailing the perfect outfit shot is confidence
Cirillo said confidence is an "underrated" element that can make someone's ensemble look even better. He prefers to take candid shots from a distance — where he can't be seen — before asking subjects for permission to share them.
"Once you stop somebody and say, 'Hey, can I take a picture,' the whole essence changes," Cirillo said. "You got to catch them off-guard ... So usually confidence translates in the way somebody's walking ... When you see it, you know it."
To replicate this technique, Cirillo told Insider you can ask a friend to take photos from different spots while you walk. He advises doing what comes naturally without repeating movements or walking through the same area more than once.
"Pick up your phone if you have to look at it for a text message or whatever and just go about your business," he said. "Candid photography to me is when you really see the real person."
Figure out what angles and lighting work best for you
While cloud cover can diffuse harsh light from the sun, Cirillo said he prefers to take photos from the shadows — where he can't be seen — because it makes editing easier for him.
"The sun's amazing and it's awesome, but it can also be really unflattering when it's coming straight down on someone's face, casting weird shadows and stuff," he said. "There's enough challenges as it is to separate people in this gigantic city ... and so with the sun involved too, I try to keep everything nice and even."
Still, Cirillo recognizes that not everyone will use his method. He suggests spending a day taking photos in different light to find your preference.
When it comes to angles, Cirillo likes to shoot "straight on," lining his shoulders up with his subject's shoulders as they walk. Because photos taken at a low angle can mess with proportions, he recommends shooting from eye level, even when you're alone.
Ultimately, Cirillo knows that self-expression through fashion and photography is a way to tell the world who you are.
"Your clothes are another way to communicate to people who you are," he said. "It's our conversation without saying anything."