Joshua Kamei, a freelance New York-based womenswear designer, was terrified the first time he stopped a woman on the street to ask, “Could you tell me more about your look?” It was just after people started to emerge from Covid lockdowns and he thought it was time to move his longtime passion of photographing New York City’s most stylish ladies to video. “It picked up,” he tells Refinery29. “And because of the number of views, I just kept doing it.”

Kamei’s account @ladiesofmadisonavenue has become a fixture of fashion TikTok, growing over 100,000 followers on the platform. His man on the street-style interviews combined with a trained eye for spotting well-dressed people have earned Kamei a unique space on the app. Not only are the women featured some of the most stylish in New York City, but they’re also older and richer than your average 20-something TikTok creator. They’re the kind of women characters like Gossip Girl’s Lily van der Woodsen and Celia Rhodes are based on. But in New York, they roam the streets, parade outside Lincoln Center, and attend galas. Much nicer than Dan Humphrey’s Gossip Girl blog, Kamei is there to document what they’re wearing: “We forget that it’s such a luxury to be in New York and people don’t see people like this quite often,” he says.

Man-on-the-street interviews have recently outpaced street style photographers in the digital fashion scene, largely thanks to TikTok, where the format has been propelled by personalities like Emma Rogue, who does outfit interviews, and Caleb Simpson, who tours strangers’ apartments. But Kamei’s videos also bring to mind the images created by Bill Cunningham, the famed New York Times photographer who made a career out of shooting street style before bloggers even existed. Much like Cunningham, who died in 2016, Kamei puts his focus on iconic women in New York, whether it’s Marilyn Kirschner, the longtime former senior fashion editor of Harper’s Bazaar, or model and activist Bethann Hardison. “Of course, he was an inspiration,” Kamei admits. “But I can never do what he has done.”

@ladiesofmadisonave I think there comes a certain point in your life that you feel you have met enough people, but that is truly a great injustice to yourself. There are so many fascinating women in the city with a lot of style. I loved meeting Maureen. She looked so elegant walking up to David Koch Theatre for a night at the ballet in her blue toile Dior skirt. @dior @nycballet. Like so many of the other fabulous women I have interviewed it isn’t just about the clothes. There is always more to these amazing women. Maureen Footer an author has written several books on Dior: “DIOR: THE LEGENDARY 30, AVENUE MONTAIGNE.” “CHRISTIAN DIOR: DESIGNER OF DREAMS.” “DIOR AND HIS DECORATORS: VICTOR GRANDPIERRE, GEORGES GEFFROY, AND THE NEW LOOK.” My advice is get dressed up got to the ballet, or the opera. Meet someone new. #dior #gasbijoux #classy #classystyle #elegant #ballet #newyorkcityballet ♬ original sound – LadiesofMadisonAve

Then again, Cunningham rarely interviewed his subjects, at least not for publication, while Kamei likes to get the behind the scenes story embedded in the women’s outfits. That’s how Kamei gets to know about gems like a head-to-toe Dior outfit at Lincoln Center worn by Maureen Footer, who authored three books on Dior. Or a grandmother-granddaughter duo spotted shopping, with the latter wearing a vintage dress from her grandmother’s collection, or a lady who opened her safe in the middle of the week to get out her “special” pearl earrings bought in Austria. Typically, he finds the women in their element: stores like Bergdorf Goodman, events like the Lenox Hill Spring Gala, or just walking down Madison Avenue. Recently, he started hanging out at Lincoln Center, where the patrons (and diehard fans) of the New York City Ballet and Metropolitan Opera like to mingle after the night’s shows. “You see some nice evening clothes,” he says. Then, there’s the biannual New York Fashion Week, where he recently spotted Carolina Herrera’s daughters sitting on the steps at the Whitney Museum, following the house’s show, like real life Blair Waldorfs and wearing matching black dresses. “That was my favorite moment,” he says. “Just seeing them sitting on the steps, it was like easy glamour.”

Kamei still finds himself surprised that his passion for documenting the style of New York women has gotten him so far online. But then again, he knows his subjects are just fascinating. “What I found is that there’s a reason they have so much style,” he says. “Clothes are the reason that I stop them, but it’s always nice when they can give you a little pearl of wisdom or something about themselves.” But he says the allure also comes from seeing New York women in their habitat. “I know that because so many people who are not from New York follow and write to me,” he says. “I almost feel like it’s our duty as New Yorkers to get dressed up.”

@ladiesofmadisonave Invisible Beauty Tribeca Premeire. “Frédéric Tcheng, the director of 2019’s Halston, returns to Tribeca with another documentary about a fashion world titan: co-director Bethann Hardison. Featuring in-depth interviews with Hardison herself, Invisible Beauty is an elegant account of the model-turned-fashion industry insider’s life and career, culminating in her tireless advocacy for more diversity both on the runway and off. 
With vibrant archival footage and access to some of the biggest names, including Naomi Campbell, Iman, and Zendaya, Tcheng and Hardison paint a picture that overflows with affection, recognizing the steps taken so others could thrive. By dwelling on Hardison’s ambition and her decades-long efforts to widen opportunities for Black people in fashion, this film is an urgent reminder that diversity is not a trend. It is an ongoing commitment that requires the kind of determination Hardison has in abundance.”—Jose Rodriguez. #bethannhardison #FrédéricTcheng #tribecafilmfestival #icons ♬ original sound – LadiesofMadisonAve

And while it requires quite a few pennies to achieve a head-to-toe Dior look, Kamei says that his videos are not just about showcasing wealth. Instead he says, it’s about showing that personal style takes time and investment to develop. Still, it sure is amusing to hear a woman say she opened her safe to wear her earrings on a random Wednesday. And Kamei knows his account wouldn’t be the talk of the town without the ladies.

“I think it says a lot that they’re willing to be put on TikTok,” Kamei says with a laugh. “I’m just so grateful to be able to talk to them.”