Kerwin Frost Sees Style as a Form of Hope

Harlem-born entertainer and street-style icon Kerwin Frost beams star-studded fashion history and charity telethons to our screens.

Darnell-Jamal Lisby

Photography by Myles Pettengill

Over even your fanciest sweatpants? We asked Kerwin Frost to self-style three pandemic fashion looks. On his return from the grocery store, Frost wears a hat by Mental, a T-shirt by Real Bad Man and MEALS pants.

For Kerwin Frost, who’s known as a talk-show host, comedian, DJ and street-style icon, style can play an integral role in connecting audiences to hopeful messages of happiness and joy in this delirious era. Growing up, he looked to figures like Missy Elliott and Mykki Blanco, who defied fashionable conventions in favor of showing their authentic selves and in so doing reshaped the way we think about the power of fashion. His own elevation as a public figure began with his association with Downtown New York street culture about a decade ago, when VFILES and Off-White were in the ascendancy. It was there that he made critical connections to lifelong collaborators like Virgil Abloh; however it was in his own neighborhood of Harlem, way uptown, that the foundations for his unique way of dressing were laid.

Speaking about his quirky ensembles from that era, he says, “When I was growing up, I wore a lot of hand-me-downs, sharing the same pair of jeans through cousins, or sneakers. I used to have to wear bigger sneakers, and now I’ll purposely wear a size 14, and I’m a size 10, to give that extra oomph and emphasize that idea of shared clothing.”

kerwin frost jumping

We’ll try anything we can just to get some sunshine during lockdown. To jump rope, Kerwin Frost wears a mask, top and pants by 69. Shoes by Adidas.

Instead of reinventing himself as his celebrity increased, and catering to the restrictive whims of the creative industries he meanders through, he transformed his struggle into an opportunity to inspire his future rather than run from it. Back when he was still in high school, he used to sneak into New York Fashion Week shows, using his style to get into these sacred bubbles covertly. “I remember going to hotel lobbies and sitting there with a suit on because I thought it was funny,” he recalls. “It’s so interesting to understand how wearing a suit changes the language of who you are.” He soon realized that he was not limited to these protocols, and that he could “mix all these things,” creating a lane for himself and others who felt similarly. Using his early brand-development experience from the Spaghetti Boys, he is now embarking on a partnership with Adidas, extending the same messages of joy and hopefulness from his persona into the clothes.

In today’s world, where learning about one another is so vital not only in an abstract sense but also to protect people from harm, Frost’s approach is to bring people together and reach out to the public. His Kerwin Frost Talks series, which he streams on YouTube, has hosted a range of stylish guests, from Shayne Oliver to Jeremy Scott to A$AP Rocky, and brilliantly uncovers fashion history interwoven with the intricacies of guests’ lives in ways that even museum curators could never evoke. Says Frost, “It’s also weird because it’s not just a designer you’ll get that information from; sometimes it’s from artists you maybe didn’t think would have a specific style, like Mac DeMarco. He has this flooded jean, cargo-jacket style he cemented, but then all the kids who looked up to him started dressing like that. I live for those moments.”

While reading—the street-style icon’s new favorite lockdown hobby—Kerwin Frost wears a vintage hat and shirt, pants by MEALS and shoes by Walter Van Beirendonck.

In Frost’s world, developing his lane and telling the stories of others who move in the same way exudes this sense of hope many people are craving. Telling these same narratives through music, after George Floyd’s death, Kerwin and his partner in love and life, Erin, produced an acclaimed 12-hour telethon to benefit Colin Kaepernick’s Know Your Rights Camp. The event brought his peers together in ways no one had thought to last year, empowering his viewers while raising funds to protect the community that raised him. Furthermore, the millennial generation and those younger have received an unfairly bad rap for not filling their predecessors’ shoes. Conversely, Frost is a shining example of these generations, building on social changes and progress by those before him, but in a way that effortlessly connects younger audiences to these ideologies and speaks to the future we are entering.

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