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Why ‘What Are You Wearing?’ Videos Are Everywhere

May 29, 2026
in News
Why ‘What Are You Wearing?’ Videos Are Everywhere

A couple weeks ago, my colleague Sandra Garcia ran around Lower Manhattan with Maurice Kamara, a.k.a. the “Hey, how ya doing today?” guy on Instagram. Sandra’s profile of Kamara, the Bill Cunningham of over-caffeinated social media fit checks, is a jolly ride. You can see why unsuspecting New Yorkers and celebrities like Michael B. Jordan are so willing to entertain Kamara’s light-touch questions about what they’re wearing.

Kamara’s story is also a poignant “only in New York” tale: After his mother died, he grew up in foster care and worked retail until he hit on the idea for his account, the People Gallery. As evidenced by his $12,000 Bottega Veneta bomber, Kamara was onto something. As he tells Sandra, “I never in a million years thought this would be my life.” The full profile is worth your time.

With more than a million followers, Kamara is the apex predator in the hunt for boisterous, man-on-the-street fits to turn into online videos. He has nabbed brand deals with Nike and Chanel, the promised land for Instagram content creators. Celebs see him as a cozy interviewer who can make them look affable without descending into any pesky P.R. minefields.

But he is scarcely the only one making fit check videos. This sort of content is all over my Instagram feed: A person behind an iPhone camera approaches a well-dressed stranger (well, we assume they’re a stranger) and asks how they look so cool or what their workout is or, most commonly, just what they have on. It may be the most popular form of fashion content online. Some of Kamara’s videos have millions of views.

A friend, visiting from Paris last week, kept making the same joke as we walked through Lower Manhattan. “What makes you confident? What are you wearing?” he’d ask, fake-filming me with his phone. The bit worked because these videos are so ubiquitous that they’re now a template, mimicked by would-be Maurices the internet over.

It’s easy to see why people like watching them. If a piece of trend analysis is a wholesome, chewy meal, the videos are little gumdrops, blooming onto our feeds. They don’t make you think any deeper, really, about why we wear what we wear, but they do tickle that most base of human instinct about clothes: If I get that jacket, I can look cool, too. Maybe even cool enough to be approached by a guy like Maurice.


Ask Vanessa

Are women’s handbags becoming obsolete? I notice they are not as popular as they used to be. Some very powerful professional women do not use them, preferring clothing with pockets and/or brief cases. Is the age of the handbag over? — Nancy, Abyhoj, Denmark

If there is one thing that is certain in fashion, it is that everything that is out comes in again, so declaring the end of any garment or accessory is pretty much a fool’s errand. But it is also true that our relationship to fashion items changes over time, and when it comes to handbags, we are at something of a pivot point. Read more …


Other things worth knowing about:

  • Henry Zankov, who makes knits patterned like “Mad Men” sofas, has been named artistic director of Diane von Furstenberg. Zankov is a canny pick. His sprightly color sense aligns with the label. Still, he’ll have a high hill to climb. DVF is a shell of its ’70s glory days. Arguably, its 79-year-old founder is more famous than the brand itself. Zankov’s first show will take place in September during New York Fashion Week.

  • Starting in 2027, Gucci will be the first luxury house to be a title sponsor of an F1 team. If you’re keeping score: Kering’s crown jewel, Gucci, is now sponsoring an F1 team. But LVMH, its corporate rival, is a partner of F1, the league. In luxury, as in auto racing, everything is a competition.

  • A new wrinkle to the Everlane saga: Michael Preysman, the co-founder who sold the brand in 2020, well before Shein bought it, has started a new venture, Still Radical. He spoke to Puck about it this week. Gotta give the man credit for jumping in while the press interest is hot.

  • Patagonia has filed a lawsuit for trademark infringement against Pattie Gonia, a drag queen-climate activist. Based on the comments on Patagonia’s recent Instagram post, people are upset about it.

  • Is every shoe designer preoccupied with toes right now? Celine’s goatskin ballet flat, with its toe-exposing slats, is obscene … yet alluring in a “can’t look away” way. Also obscene? The $2,950 price tag.

  • If any of you get married in the Stussy tuxedo jacket this summer, please send me a photo. Streetwear, it’s all grown up!


Look of the week

Jacob Gallagher is a Times reporter covering fashion and style.

The post Why ‘What Are You Wearing?’ Videos Are Everywhere appeared first on New York Times.

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