Fashion of the 90s and early 2000s: Justin Timberlake’s y2k menswear in *NSYNC and the couple dressing with Britney Spears

From “Goodbye! Goodbye! Goodbye!” for Justified, Justin Timberlake penned the plan for the boy band star. The singer began his musical career in the late 90s as the fifth of the pop group *NSYNC. By the turn of the millennium, the group had risen to the top of the Pop2K charts, even surpassing the Backstreet Boys with their record album. No strings attached. *NSYNC was the boy band and Justin, its unofficial leader. While the band was burning brightly, however, two years later they were put on ice, and Justin rose to stardom with the smash hit of 2002. Justified.

Justin epitomized the boy band look of the year 2000: a flashy, larger-than-life version of menswear that drew inspiration from both euro-trash, streetwear and kitsch Americana. Think Canadian tuxedos, dazzling bandanas, faded aviators, denim fedoras and metallic jumpsuits. Here, we take a look back at some of the singer’s most iconic outfits from the ’90s and early ’00s.

In the clip “I Want You Back”, 1998

Did you know that NSYNC debuted in Germany? After forming in the United States, the band signed with a Munich label and recorded their entire debut album in Sweden with producers Max Martin and Andreas Carlsson. The band released NSYNC in Germany in 1997, becoming an overnight hit across Europe, although the album would not reach the United States for another year. * NSYNC’s European origins begin to make sense when you step back into their early career attire. Take the music video for “I Want You Back,” for example, where the boys give their best Tour de France in a series of coordinating Spandex half-zip zips.

Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images.

At the American Music Awards, 1999

Big events call for even bigger outerwear. Justin and his *NSYNC bandmates arrived at the 1999 AMAs to scoop the award for Favorite New Pop Artist in a series of ostentatious jackets. Joey wore red leather, Lance wore laminated corduroy, and Justin wore a metallic blue jumpsuit.

*NSYNC at the VMAs in 2000

Photo by Ron Galella/Ron Galella Collection via Getty Images.

At the VMAs, 2000

Of course, *NSYNC saved their most daring outfits for the VMAs. In 2000, the group stopped by the infamous awards show red carpet wearing a motley array of bedazzled and bespectacled looks. Special mentions go to JC’s metallic snakeskin pants and Lance’s Guy Fieri cosplay, however, Justin really steals the show in a pair of patchwork ostrich leather pants, cowboy boots and a turtleneck. transparent white.

*NSYNC performing at Madison Square Garden in 2000

Photo by KMazur/WireImage.

Performing at Madison Square Garden, 2000

* NSYNC’s MSG concert was the hottest ticket of the summer of 2000. The concert took place just months after the band dropped the best-selling record No strings attached. “Bye! Bye! Bye!” was all over the air and *NSYNC was, in fact, the biggest boy band in the country. Here, the band performs in a series of matching stage costumes, which draw inspiration from the outsized and colorful fashions of New Jack Swing and Michael Jackson (note the gloves.) Justin stands out from the crowd in a bedazzled bandana, which speaks from the Americana-y glitz of Y2K’s McBling look.

Britney Spears and Justin Timberlake at the American Music Awards in 2001

Photo by Jeffrey Mayer/WireImage.

At the American Music Awards, 2001

Here’s the most iconic couple’s outfit of all time. In 2001, American pop star Britney Spears and her then-boyfriend Justin created glamorous American-style workwear in a pair of denim formal looks. While Britney covered her deconstructed denim dress with rhinestone accessories, Justin gave new meaning to the phrase “Canadian tuxedo” in a denim suit.

Britney Spears and Justin Timberlake at a celebrity basketball game in 2001

Photo by Ethan Miller/Getty Images.

At a celebrity basketball game, 2001

The AMAs wasn’t the last time Britney and Justin stepped out in pairing looks. Later that year, the teenage pop duo attended *NSYNC’s charity basketball game in a matching jersey set. Justin reads “Stinky” and Britney, “Pinky”.

Justin Timberlake at a post-VMA party in 2002

Photo by Dimitrios Kambouris/WireImage.

At the post-VMA party, 2002

Here, Justin gives us a more understated (but no less sleazy!) take on early 2000 McBling fashions. You won’t see a Von Dutch cap or dazzling denim in Justin’s 2002 post-VMA outfit. You will, however, notice a fuzzy fedora and a Coors Light t-shirt worn with a “suit and tie.”

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