For New Yorkers, fashion inspiration can be found on a walk through Central Park or a ride on the subway. For those outside the city, there are street-style social media accounts like Watching New York, NYC Looks, and OOTD showing the trends emerging in New York and beyond.
“People like a New York City voyeuristic experience,” Johnny Cirillo, photographer and creator of Watching New York, told us.
Brands are taking notice. In recent months, Watching New York, which has more than 2 million followers on Instagram and TikTok combined, has worked with brands like Aerie, Lego, and JD Sports. OOTD, which has more than 400,000 followers across both platforms, has also posted organic-looking street-style content with brands like Free People, Rothy’s, and Cult Gaia that have generated thousands of likes on TikTok and Instagram.
Informal, documentary-style depictions of everyday style seem to be a hit with consumers, whether or not the content is branded. “People want that relatability,” Cory Muroff, co-founder of OOTD, told us. “We’re seeing a big shift in the way that people consume content, and this style is working very well.”
Stacey McCormick, CMO of Aerie, agreed: “Street-style photography is the ultimate trend report,” she told us via email. “The rise of creator-led content and the shift toward organic, community-driven marketing make this an area with significant potential for brands looking to connect with their audience in a fresh, engaging way.”
Candid or branded?
OOTD, which secured its Instagram handle in 2017, started breaking into branded posts last summer. Its first post was with Free People in July, Muroff said, a few months after OOTD started a TikTok account and opened the website ootd.com, where it has recently begun experimenting with shoppable gift guides.
Capturing trends in action means shooting footage on the streets of New York nearly every day, sometimes all day, and sifting through thousands of videos, Muroff said; about 90% of the footage OOTD posts are candids of people unaffiliated with the account. Branded videos are designed to appear just as candid, Muroff said, so it feels “as if it wasn’t staged at all.” Alex Rogers, OOTD’s other co-founder, said branded posts often feature friends or everyday people wearing a brand’s clothes instead of recognizable models or influencers—assuming the brand partner has given them that leeway.
“We’ve been super thankful to have a ton of creative freedom to match the style that we do organically,” Rogers told us.
One recent partnership video with Sneex, which shows women walking around SoHo in high-heeled sneakers, has generated more than 2 million views and 70,000 likes on TikTok, which Muroff said is entirely organic.
Keeping it real
Watching New York also got its start around 2017, but it wasn’t until 2020 when Cirillo started incorporating branded content into the account, starting with a Pandora partnership. “They asked me if I would mind putting a necklace on somebody, take a picture of them with it, and put it on my page,” he said. “I said, ‘Well, how much?’ And they gave me a number. And I was like, ‘Holy cow.’ I quit my job, got an agency right after that, and I’ve been doing it since.”
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Cirillo says he now inks two or three brand deals every month, and often recruits strangers he’s captured in organic shoots for branded campaigns based on their style. Other times, brands might present brand ambassadors who Cirillo may review and incorporate into shoots based on how well they “represent the people of New York,” said Shoshannah Cutler, who works with Cirillo on brand partnerships as CEO, founder, and creator manager of Shoshalmedia.
Like OOTD, the account generally steers clear of models or creators and is careful to feature styles that are the right fit. “The idea of a post is to get as many eyeballs on the content as humanly possible,” Cirillo said. “When [the models] all look kind of similar…and it’s clothing and style that I don’t usually post, I think I lose the audience that way.”
Watching New York has also shot candid-style photos for brands like Aerie to use on their owned accounts. McCormick said street-style shoots can “spotlight the diverse ways [its] community styles the brand,” while also helping to keep the brand culturally relevant.
Rogers said he plans for OOTD to begin producing candid-style content for brands’ owned channels.
Taking it to the streets
While there’s “no blueprint” to Watching New York’s brand work, Cirillo said he’s seen success when brands “almost gloss over” a product, like subtly mentioning or showing it in a man-on-the-street interview, as opposed to heavily focusing on the item. As for showing one product on many people or many products on one person? It all depends on the brand, he said.
“Anything that we’ve done that was much higher end, people love seeing head-to-toe,” he said, citing a 2022 Gucci x MLB collaboration he photographed as one example. “When it’s other products that are more affordable, I think people like being like, ‘Oh, I wouldn’t have thought to put that shoe with this outfit.’”
Cirillo has also branched out into brand event photography, which he did for Aerie in December. McCormick said guests at the event were “genuinely excited” to be photographed by Cirillo, and that those photos helped amplify the brand’s presence across social media. Aerie and Cirillo also worked together on a recent on-the-street shoot for the brand, which McCormick compared to user-generated content, calling it an “extension” of the strategy.
The street-style content, she said, “allows us to engage our audience in a way that feels natural, aspirational, and highly shareable—bridging the gap between editorial storytelling and everyday fashion inspiration.”
While Cirillo said he can sometimes “feel the pressure of…‘selling out’” when working on branded posts, he said he keeps them spaced out and in line with his overall look in an effort to satisfy his followers while continuing to run the account full-time.
“You got to look at it as a commercial in a TV show,” he said. “These are the commercials. Bear with me.”