Usher Explores Iconic Looks From the Last 27 Years, From His First Album Cover to the 2024 Super Bowl

“I was 15 years old, doing my first album in New York City, and I decided I wanted to do things my way,” Usher tells Vogue as he revisits the cover art from My Way, which was released in 1997. This was the first of many iconic looks the singer-songwriter and performer has worn over the last 20-plus years, leading up to some of his most recent ones: the custom designs he slipped into for the 2024 Super Bowl.

From award shows to his Las Vegas residency, Usher never shied away from out of the box fashion; in particular, he references his look from the 2000 Teen Choice Awards. He claims that that was the year he started to really take off–symbolized by the fact that he had two “U” chains dangling from his neck on the carpet. “What did you wear? My six pack!” he laughs, showing Vogue a photo of him in a one-of-a-kind Gucci coat, with no shirt on underneath.

Once he reached the 2020s, Usher shared that everything was starting to unfold: his two-year residency, his digital Vogue cover, and being the Super Bowl halftime performer. “I found out I was going to be the Super Bowl halftime [performer] by Jay-Z,” he says. “He asked me, ‘Are you ready for the major moment?’ and I was like ‘The Super Bowl? Hell yeah!’” Usher worked with his stylist, Jeremy Haynes, to design “the entire collective of skating culture” for that opening moment. He adds that every outfit he wore during the show had tributes designed into them–noting that his athletic gloves were a nod to Michael Jackson.

As for a more recent fashion highlight, Usher recalls his 2024 Met Gala look; he wore an Alexander McQueen cape with laminated roses to give the impression that he was the “villain,” among those who came dressed with more whimsy.

Above, watch Usher’s full Life in Looks video.

Director: Gabrielle Reich
Director of Photography: Mike Lopez
Editor: Evan Allan
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