22 Usher Outfits That Define His Style, From the Met Gala to the Skating Rink

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 just released a new single, “Good Good,” and is set to perform in Paris in September in a special eight-day residency. Titled “Rendez-Vous Á Paris,” the festivity will take place from Sept. 24 to Oct. 5, and it coincides with Paris Fashion Week, which is so fitting for Usher. 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 of his special Parisian fête, let’s take a look at some of Usher’s most memorable fashion moments.

Related: Usher Responds to Keke Palmer Vegas Drama: “You Can’t Beat the Internet”

Courtesy of Rémy Martin / Greg Doherty

Usher at Rémy Martin x Usher “4 on the Floor” Event

For the Rémy Martin x Usher “4 on the Floor” Roller Skating Pop-up, Usher tapped into his classic, collegiate-inspired style wearing a red bomber jacket with white sleeves, a white T-shirt, and denim shorts. With his black-and-red roller skates on his feet, he delivered a captivating skate performance while guests mingled, enjoyed sounds curated by Ladies Love R&B, and perused limited-edition Rémy Martin x Usher x Jon Stan merchandise.

Getty / Jeff Kravitz

Usher at the Met Gala, 2023

Usher collaborated with British menswear designer Bianca Saunders for his 2023 Met Gala look. The suit takes inspiration from Karl Lagerfeld, who inspired this year’s theme, while still feeling quintessentially Usher.

Getty / Frank Micelotta

Usher Performing at Live Showtime Concert, 2005

The “U Remind Me” singer was known for his aesthetic of oversize jerseys, headband, and his signature “U” chain in the early ’00s.

Getty / Frank Micelotta

Usher Performing at Live Showtime Concert, 2005

This bedazzled suit channels Michael Jackson and Usher‘s performance aesthetic in the early ’00s.

Getty / J. Merritt

Usher at the MTV Video Music Awards, 2005

Duality is a key component of Usher‘s style. He can go from streetwear to dapper suits with ease.

Getty / Dan Kitwood

Usher in London, England, 2008

Much like his idol Michael Jackson, Usher often was inspired by military gear, making these jackets a staple throughout the ’00s.

Getty / Patrick McMullan

Usher at an Yves Saint Laurent x Bergdorf Goodman Party, 2005

His style also dabbles into a preppy Americana aesthetic. Here, he pairs a pilot leather jacket with a white button-up shirt, denim, and boots.

Getty / Steve Granitz

Usher at Movies That Rock, 2007

Another example of him playing with a preppy aesthetic, opting for a suit, sans the jacket, and wearing a newsboy cap.

Getty / Arnaldo Magnani

Usher at Victoria's Secret Fashion Show, 2005

His wardrobe staples in the early aughts? A blazer, a button-up shirt, and denim.

Getty / Bryan Bedder

Usher Filming Promo for MTV Movie Awards, 2008

Here, Usher is seen channeling his inner James Bond, looking dapper in a smart tuxedo.

Getty / Taylor Hill

Usher at the Ripple of Hope Awards, 2017

The format for most of his outfits are the same: a statement jacket, a T-shirt or button-up shirt, a trouser, and either a sneaker or a boot. This Haider Ackermann bomber jacket became a signature of his throughout the 2010s.

Getty / Axelle/Bauer-Griffin

Usher at the LACMA Art + Film Gala, 2017

Here the R&B superstar is all dressed up to celebrate excellence in art and film at the 2017 LACMA Art + Film Gala.

Getty / Pascal Le Segretain

Usher at Chanel Spring 2017 Runway Show

Usher is seen wearing full head-to-toe Chanel at the brand’s infamous “Data Center Chanel” show.

Getty / Gary Gershoff

Usher at the 48th Songwriters Hall of Fame, 2017

Usher looks stylish yet laid-back in a pink bomber jacket, a button-up shirt, denim, and a coordinating loafer.

Getty / JEAN-BAPTISTE LACROIX

Usher at the Vanity Fair Oscar Party, 2020

Always one for supporting Black designers, he opted for a Balmain suit designed by Olivier Rousteing for the 2020 Vanity Fair Oscar Party.

Getty / Lionel Hahn

Usher at the Vanity Fair Oscar Party, 2023

At the Vanity Fair Oscar Party in 2023, Usher wore a slightly boxy white suit.

Getty / Pascal Le Segretain

Usher at the Balmain Fall 2021 Runway Show, 2020

As part of the Balmain army, Usher wore a full ensemble by the French fashion house to the runway show in Paris.

Getty / Gotham

Usher at a Met Gala Afterparty, 2023

After the show, it’s the after party – and once again working with Bianca Saunders, Usher wore a mesh long-sleeved shirt with oversize gray trousers and pearls for post–Met Gala soirees.

Getty / Pierre Suu

Usher at the Wales Bonner Fall 2023 Show, 2023

Wearing Wales Bonner, of course, Usher is the epitome of cool in a black-and-white bomber jacket and trousers, with his ginger-red hair providing a pop of color to his ensemble.

Getty / Pierre Suu

Usher at the Amiri Menswear Fall 2023 Show, 2023

As part of his mens Paris Fashion Week takeover, Usher attended the Amiri show looking incredibly sleek in all-black separates, bold jewelry, and white sneakers.

Getty / Taylor Hill

Usher Performing at The Roots Picnic, 2023

Keeping with earlier stage-outfit formulas, he wore a leather bomber and leather trousers to perform to a sold-out crowd at the 2023 Roots Picnic festival.

Getty / Kayla Oaddams

Usher Performing at the Roots Picnic, 2023

The full leather, the ATL hat, the “U” chain: this outfit is giving throwback, quintessential Usher, but make it 2023.

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