Justin Bieber has spent the past decade and a half becoming one of Hollywood’s most eccentric (and GQ’s most celebrated) dressers, an accolade he earned in no small part thanks to superstar celebrity stylist Karla Welch, whom the Canadian pop star began working with in 2011. Back then, Bieber entered his post-teen-heartthrob era with a gonzo—and, at times, perilous—new lease on life, which was accompanied by a boundary-pushing new wardrobe.
Under Welch’s fashion tutelage, Bieber went, as Welch told The New Yorker in 2019, “full Hunter S. Thompson.” He started showing up at ritzy locales, such as the the Beverly Hills Hotel or a Michelin-starred restaurant, wearing oversized Hawaiian shirts, expensive flip-flops, and designer sweatpants five sizes too big, and for at least the last decade, never stopped. Welch even began dressing Justin’s wife, Hailey Bieber, for certain events, including the couple’s memorably mismatched ensembles at the 2022 Grammys. Together, the Biebers became two of the most interesting, and influential, trendsetters in the biz. As Welch told The New Yorker, “I always say that Justin was the best teacher I had.”
However, for the past several months, Bieber has been working with another stylist, Jenna Tyson, as confirmed on Tuesday in a joint-shared Instagram post from the fashion-news account Up Next. According to the post, Tyson joined Bieber’s styling team “as the newest clothing sourcer [and closet] curator, working alongside him as he styles the looks himself.” It appears Tyson, who also works with NBA star James Harden, began dressing JB as early as last October, when the singer accompanied Hailey to an event dressed in an unbuttoned Celine flannel shirt, roomy Margiela jeans, and a jaunty Western hat. Over these first few months of 2025, during which Bieber has reportedly been recording new music, the singer has worn a parade of extremely baggy pants, workwear-inspired jackets, and designer accessories; for example, on Monday, he was spotted in a boxy Willy Chavarria work shirt, distressed 424 jeans, and fingerless leather gloves. Nothing too far off from his usual fare—but again, per the news post, the singer has been styling himself, with Tyson assisting on the sourcing.
According to a 2022 Huffington Post interview, Tyson is a native of Orange County, California, who moved to New York City to study millinery at the Fashion Institute of Technology, while also enrolling in the Misa Hylton Fashion Academy mentorship program in 2012. Over the next decade, she worked as an assistant stylist with Missy Elliott, Future, Gunna, and Roddy Ricch before landing her first big solo client, the Alabama-born rapper Flo Milli, in 2022.
“Jenna is the Future of Fashion happening now in real time,” Hylton wrote in a since-deleted Instagram post congratulating Tyson on her new gig with Bieber, whose personal style has long drawn on hip-hop fashion trends such as the ones Hylton spearheaded in the 1990s and early 2000s, when she styled the likes of Mary J. Blige, Lil’ Kim, Jodeci, and Diddy.
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