From Timberlands and Nikes to high fashion labels like Balenciaga and Prada, Usher's wardrobe has been through a fanatically twisted rollercoaster ride over the years. The singer came onto the scene in the '90s rocking baggy jeans and suits that made us question his celebrity status, but over the years this R&B star has developed his own signature look, rendering him a modern day fashion icon. Click through our sartorial time machine and check out Usher's fashion evolution!
Who is this mysterious man in black? ...
Who is this mysterious man in black? Usher was riding a fast-moving comet to fame as he strutted down the red carpet at the 8th annual Billboard Music Awards on December 8, 1997 in a head-to-toe black look topped with a black knit cap.
Who needs a shirt when you have abs l...
Who needs a shirt when you have abs like Usher's? During the 2000 Teen Choice Awards in Santa Monica, Cali., Usher arrived shirtless in a white fur jacket, white cap, and majorly blinged-out necklaces.
Still covered in bling and fur, Usher...
Still covered in bling and fur, Usher added a shirt to his baller look as he strutted down the red carpet at the 2000 Radio Music Awards in Las Vegas.
It's safe to say that Usher is not BF...
It's safe to say that Usher is not BFFs with PETA. The singer swapped out his fur jacket for an all leather ensemble at the 2001 MTV Video Music Awards. He completed his leather look with an Aaliyah printed T-shirt.
After winning Best Male R&B Artist at...
After winning Best Male R&B Artist at the 2002 BET Awards, Usher looks dapper, posing yearbook picture-style in a white suit and pink tie.
Perhaps we spoke too soon. Usher look...
Perhaps we spoke too soon. Usher looked like he ransacked his older, and much larger, brother's closet during Billboard's 2002 R&B Hip Hop Awards, wearing a jumbo, shapeless polo and hefty, tailored jeans.
Business on top, party on the bottom!...
Business on top, party on the bottom! Usher rocked a slick shirt and vest paired with baggy jeans at Stella McCartney's store opening party in September 2002.
During a 2003 Grammy pre-party at NYC...
During a 2003 Grammy pre-party at NYC's Show nightclub, Usher wore a pinstriped suit and tie with a matching fedora. Someone needs to remind this singer that he is an R&B star, not a school teacher.
Losing the tie and gaining a pair of ...
Losing the tie and gaining a pair of shades, Usher explored the world of fashion for a style that blends his love for suit attire with a his baller swag as he posed with Chili of TLC during the 2003 BET Awards in Hollywood.
A casual and cool Usher appeared on M...
A casual and cool Usher appeared on MTV's TRL at the MTV studios in Time Square March 23, 2004. We are still undecided on whether we love or hate that green and yellow color-blocked jacket. What do you think?
The suit Usher wore to the 2004 Teen ...
The suit Usher wore to the 2004 Teen Choice Awards in California may have looked like he borrowed it from his grandfather, but that fabulous bright orange lining more then made up for the dull plaid exterior.
What better way to honor the great Ra...
What better way to honor the great Ray Charles at the Genius: A Night For Ray Charles event than in a lush burgundy velvet suit and a pair of killer aviators?
Keeping with the velvet look, Usher l...
Keeping with the velvet look, Usher looked icy fresh in this all-white ensemble, topped off with a teal velvet blazer, at the 2005 post-Grammy party in L.A.
Usher took a huge fashion tumble at t...
Usher took a huge fashion tumble at the 2005 MTV Networks UpFront event in NYC, wearing ill-fitting jeans, a bizarrely printed untucked tie, and a leprechaun green sweater. This is by far the worst we have seen yet! It can only get better from here, right?
Now this is how to successfully rock ...
Now this is how to successfully rock a green sweater! Usher looks minty fresh in all white and a green knit at Glamour's 2005 Women Of The Year Awards in London.
Usher blended Mr. Gatsby's style with...
Usher blended Mr. Gatsby's style with that of the Easter Bunny as he arrived at the Philanthropic Arts Foundation's 2005 'Art For Life' benefit in East Hampton. Here comes a well-dressed Peter Cottontail, in a pastel pink shirt, pale blue tie and lavender sweater!
Usher's love for velvet made a triump...
Usher's love for velvet made a triumphant return during the 2005 Black Ball hosted by Alicia Keys at New York's Lincoln Center. The singer rocked a sophisticated, unfussy look with a deep blue, velvet blazer, light blue turtleneck, and jeans. The jeans are still a bit big, but at least the jacket distracts from the baggy bottoms.
Usher looked polished and refined in ...
Usher looked polished and refined in a black tuxedo and white bow tie at the 2006 Mercedes-Benz Presents the 17th Carousel of Hope Ball in Beverly Hills.
Still refined but a bit too conservat...
Still refined but a bit too conservative for our taste, Usher arrived at Conde Nast Media Group's 2007 Movies Rock event in a gray vest, with matching trousers and green tie.
Looking like he stepped right off the...
Looking like he stepped right off the pages of GQ, Usher attends the magazine's 2008 Gentlemen's Ball in New York City, wearing a lavender sweater and grey slacks.
Usher finally rocked a three-piece su...
Usher finally rocked a three-piece suit at the 2008 Victoria's Secret Fashion Show in Miami Beach, Florida. Perhaps it just took the help of some very pretty angels to get his style on track.
And a few months later, the style suc...
And a few months later, the style success was gone, as Usher arrived at the Palms Casino Resort's Playboy Club in 2009, wearing a dull and clashing patterned look.
BEVERLY HILLS, CA - JANUARY 30: Singe...
BEVERLY HILLS, CA - JANUARY 30: Singer Usher arrives at the 2010 Pre-Grammy Gala & Salute To Industry Icons at Beverly Hills Hilton on January 30, 2010 in Beverly Hills, California. (Photo by Jeffrey Mayer/WireImage)
Looking debonair and chic, Usher perf...
Looking debonair and chic, Usher performs onstage on ABC's "Good Morning America" on March 30, 2010 in a tailored black suit, leather gloves and black cap.
Drenched in black leather, Usher arri...
Drenched in black leather, Usher arrives at the 2010 American Music Awards in L.A. The star blended hot S&M style with an elegant sophistication.
Usher paired a blue leather jacket wi...
Usher paired a blue leather jacket with green combat pants and a striped T-shirt for a chic, unfussy look as he arrived at an L.A. Belvedere launch party in 2011.
Walking the streets of New York with ...
Walking the streets of New York with son Usher Raymond V in 2011, the superstar looks casual but slick in a tight and bright tee, jeans and a pair of matching kicks. Usher Jr. looks pretty styling himself!
Looking spruce and nonchalant in a he...
Looking spruce and nonchalant in a head-to-toe Dior ensemble, Usher attends the Dior Homme Menswear Spring/Summer 2012 show as part of Paris Fashion Week.
Usher tours the trading floor at MTV'...
Usher tours the trading floor at MTV's 30th Birthday celebration at the New York Stock Exchange in 2011. Who knew a cardigan could look so cool?
The "Scream" singer made us want to d...
The "Scream" singer made us want to do just that in this debonair and sultry look, which is our favorite overall. Usher rocked a perfectly-fitted black tuxedo with a whimsical floral shirt at the 2011 Pencils of Promise charity gala in New York City.
Usher brought the cool blues to the w...
Usher brought the cool blues to the white carpet in a cerulean blue suit at the 2012 Billboard Music Awards in Las Vegas. He paired the bright blue with a denim shirt and grey oxfords, finally learning how to blend his love for the suit with his sparkling celebrity charm.