At the tender age of 15, while recording his debut album in New York City, Usher made a bold decision: he would do things his way. This determination, reflected in the cover art of his 1997 album “My Way,” marked the beginning of a long and illustrious fashion journey. Over the past two decades, Usher has consistently pushed boundaries, captivating audiences with his out-of-the-box style, from award shows to his Las Vegas residency.
One look that stands out is his outfit from the 2000 Teen Choice Awards. Usher credits this moment as the start of his meteoric rise, symbolized by the two “U” chains adorning his neck. He playfully recounts the look, quipping, “What did you wear? My six pack!” A photo reveals him in a unique Gucci coat, confidently baring his torso.
As Usher transitioned into the 2020s, his career reached new heights. He landed a two-year residency, graced the digital cover of Vogue, and was chosen to headline the Super Bowl halftime show. “I found out I was going to be the Super Bowl halftime [performer] by Jay-Z,” he reveals. “He asked me, ‘Are you ready for the major moment?’ and I was like ‘The Super Bowl? Hell yeah!’”
For this momentous occasion, Usher collaborated with stylist Jeremy Haynes to create a performance that embodied “the entire collective of skating culture.” Each outfit featured subtle tributes, like his athletic gloves, a nod to Michael Jackson.
Looking back on more recent fashion highlights, Usher recalls his 2024 Met Gala ensemble. Dressed in an Alexander McQueen cape adorned with laminated roses, he aimed for a “villain” aesthetic amidst the whimsical attire of his fellow attendees.
Watch Usher’s full “Life in Looks” video to see his remarkable style evolution unfold.
