Usher Styles a Tweed Blazer With Pearl Necklaces at the

Usher, fresh off the heels of his sold-out, highly publicized Las Vegas residency “My Way” at the Park MGM, shows no signs of letting up. On top of an interactive partnership and activation with Rémy Martin, he recently released a new single, “Good Good,” and is performing in Paris in September in a special eight-day residency. Titled “Rendez-Vous Á Paris,” the festivity is taking place from Sept. 24 to Oct. 5, and it coincides with Paris Fashion Week, where Usher has delivered one bold fashion moment after another. Throughout the course of his three-decades-long career, the R&B sensation has been a fashion favorite. From starring in Tommy Hilfiger campaigns in the ’90s to wearing full head-to-toe Rick Owens to rubbing shoulders with Kim Jones and frequenting Paris Fashion Week, Usher’s style impact can’t be understated.

The “My Boo” singer and fashion icon burst onto the scene in the early ’90s, wearing exaggerated, oversize suits and jeans, Timberland boots, and jerseys. Soon, his style developed further into classic tailoring and blazers paired with jeans, exploring the intersection of hip hop and high fashion. Haider Ackermann bomber jackets with sneakers, Chanel tweed jackets with grills, and custom leather Balmain suits: Usher embraced fresh-off-the-runway fashion while staying true to his signature aesthetic. In fact, at the fall 2023 Paris men’s collections, all eyes were on Usher. Showcasing the full breadth of his fashion sense, he sat front row at highly anticipated shows like Commes des Garçons and Amiri, wearing highly stylized outfits and debuting a new ginger hair color.

Throughout his career, Usher has always prioritized Black design talent and stylists, attending the shows of Wales Bonner and Bianca Saunders. Speaking of Saunders, at this year’s Met Gala, themed “Karl Lagerfeld: A Line of Beauty,” Usher stole the show wearing a custom suit by the British designer. Saunders, an emerging design phenomenon, orchestrated a smart menswear look for the crooner that perfectly fit the brief — honoring the contributions of Lagerfeld — while pushing the bounds of mens tailoring. Since then, Usher’s developed a designer/muse relationship with the 2021 Andam Fashion Award winner.

Ahead, let’s take a look at some of Usher’s most memorable fashion moments.

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