With singer opening up to Details about his boy-band fashion mistakes, MTV News rounds up his most regrettable looks.
By Jocelyn Vena
Britney Spears and Justin Timberlake in 2001
Photo: Jeffrey Mayer/ WireImage
Justin Timberlake definitely looks very different now than he did back in his 'NSYNC days. Back then, his style mostly consisted of ill-fitting leather jackets, baggy trousers and that famous head of unkempt blond curls.
Those clothes and even that fro were definitely the "in" things. It was the late 1990s and early 2000s, so that meant neon tracksuits, sunglasses with rose-colored lenses and loose-cut JNCO jeans were all the rage. Therefore, we're thinking that Justin should probably go a little easier on himself when reflecting on the fashion risks he took back in the day.
But in a new interview with Details magazine, Timberlake revealed his true feelings about some of his cringe-worthy looks. "There were many moments in my teenage years where I succumbed to, um, the weirdness of the group I was in. And in trying to conform — we're marionettes! — I ended up looking like a moron."
Things began to take a turn for the better after he shaved off his curls. "A shaved head. It's scary the first time you do it, because you don't know what's under there — you could have some weird knot — but a shaved head is just so easy," he said.
Check out photos of Justin Timberlake's Questionable Fashion Choices
While Timberlake may not like to think about the past, MTV News is looking back on some of Timberlake's most questionable 'NYSNC looks.
1999 Billboard Music Awards At the show, his sunglasses had purple lenses, he was rocking a major medallion on his chain and every guy in the band had some version of an all-black leather suit with a racer stripe on it. For the record, Timberlake's was right across his chest.
1999 American Music Awards Nothing says "I'm attending a major awards show" more than a casual gray mock turtleneck, a blinging chain and a shiny turquoise raincoat with drawstring waist, right?
2000 Puppet Unveiling Going for a casual, cool look at the unveiling of the band's No Strings Attached-inspired puppets, Timberlake's gray and blue baseball T-shirt was perfectly accessorized by that giant out-of-hand 'fro atop his head. While Timberlake later shaved it off, the puppet is stuck with that look for all of eternity.
2000 Wango Tango Concert Cornrows and aviators with red lenses? We assume no further explanation is needed.
2001 American Music Awards A denim suit and cowboy hat was made even better thanks to Britney Spears' matching strapless denim gown. It was baffling at a time when perplexing style was all the rage. To be a fly on the wall as a stylist convinced two of the biggest pop stars in the world to wear those outfits!
Voting in the Final Four of MTV's Battle of the Boy Bands runs until noon ET on Friday, May 4. Winners are determined by fan votes, so if your favorite band made the cut, make sure you keep voting. Tune in to AMTV and MTV Hits for their boy-band video takeovers each day and make sure to spread the word on Twitter using the hashtag #BBB and like us on Facebook for updates!
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