Getty | Pascal Le Segretain

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.

Getty | Stephane Cardinale – CorbisUsher at the Chanel Show During Paris Fashion Week, October 2023

Usher rounded out his Spring 2024 Paris Fashion Week appearances at the Chanel show, wearing one of the house’s signature tweed jackets paired with a white button-down shirt, black pants, and layers of pearl necklaces.

Getty | Pascal Le SegretainUsher at the BoF 500 Gala During Paris Fashion Week, September 2023

Dressed in Louis Vuitton designed by Pharrell, Usher wowed in a kilt, a cropped jacket, and a pearl-embellished hat on the red carpet at the BoF 500 Gala.

Getty | Jacopo RauleUsher at the Valentino Show During Paris Fashion Week, October 2023

Usher was the epitome of sleek and cool at the Valentino show during Paris Fashion Week, wearing light denim jeans and a matching long jacket, paired with a white button-down shirt and a black skinny tie. He completed the look with black shades and silver cap-toe loafers.

Getty | Marc PiaseckiUsher at the Balenciaga Show During Paris Fashion Week, October 2023

Embracing a signature Balenciaga aesthetic, Usher posed in a black cutout mask with an oversize jacket, leather pants and boots, and a silver “U” chain outside the Spring 2024 show.

Getty | Pascal Le SegretainUsher at the Marni Show During Paris Fashion Week, September 2023

Usher made a bold sartorial statement at the Marni Spring 2024 show, wearing a red coat-and-pants set covered in black polka dots, styled with matching red separates and sneakers.

Courtesy of Rémy MartinUsher at Rémy Martin x Usher “4 on the Floor” Event, July 2023

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 KravitzUsher at the Met Gala, May 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 MicelottaUsher Performing at Live Showtime Concert, March 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 MicelottaUsher Performing at Live Showtime Concert, March 2005

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

Getty | J. MerrittUsher 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 KitwoodUsher in London, England, May 2008

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

Getty | Patrick McMullanUsher at an Yves Saint Laurent x Bergdorf Goodman Party, November 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 GranitzUsher at Movies That Rock, December 2007

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

Getty | Arnaldo MagnaniUsher at Victoria’s Secret Fashion Show, November 2005

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

Getty | Bryan BedderUsher Filming Promo for MTV Movie Awards, May 2008

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

Getty | Taylor HillUsher at the Ripple of Hope Awards, December 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-GriffinUsher at the LACMA Art + Film Gala, November 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 SegretainUsher at Chanel Spring 2017 Runway Show, October 2016

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

Getty | Gary GershoffUsher at the 48th Songwriters Hall of Fame, June 2017

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

Getty | JEAN-BAPTISTE LACROIXUsher at the Vanity Fair Oscar Party, February 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 HahnUsher at the Vanity Fair Oscar Party, March 2023

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

RELATEDFrench Manicures With a Twist Ruled the Met GalaGetty | Pascal Le SegretainUsher at the Balmain Fall 2021 Runway Show, February 2020

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

Getty | GothamUsher at a Met Gala Afterparty, May 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 SuuUsher at the Wales Bonner Fall 2023 Show, January 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 SuuUsher at the Amiri Menswear Fall 2023 Show, January 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 HillUsher Performing at The Roots Picnic, June 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 OaddamsUsher Performing at the Roots Picnic, June 2023

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