…but later evolved into a sleek rockabilly vixen, who’s somehow defied laws of aging over the past 20 years.
Most iconic fashion moment: Definitely 1998’s blue hair and blue shag bra. The questionable bindi and jewel art aside, Gwen made a lasting impression as a darling ska punk who’d get on the ground and do push-ups at a moment’s notice.
3. Justin Timberlake went on his own remarkable journey, somehow moving from ramen hair and cozy cable knits to tie-dye jeans and an oh-so-sexy buzzcut.
But just one year later, it was a whole new Justin and a baby step into the word of suits and ties we now associate with him. (He’s still rocking the fedoras, though.)
Most iconic fashion moment: 2002’s “Like I Love You” outfit marked Justin’s coming-out as a solo artist and the first step into developing his own style. That red shirt and matching red-striped fedora is forever burned in our collective memory as the moment “Justin” graduated to “JT.”
5. Believe it or not, Busta’s always been killing it on the red carpet, turning even subtle accessories — like his pager and flip-phone — into a bold fashion statement.
Most iconic fashion moment: Busta’s red and gold outfit (is that a kimono? salwar kameez?) had shoes to match and made for the most unforgettable outfit to stand next to Martha Stewart in. It was bold. It was colorful. It was confusing. It was Busta.
6. The evolution of Mariah into a full-on diva in this photo set is incredible. More skin, more glitz, more glam!
Most iconic fashion moment: You can’t beat Mariah’s “Honey, I’m free” debut; her midriff-baring black number signaled the arrival of a whole new Mariah, finally free from the controlling hand of Tommy Mottola, ready to live her own damn life.
7. Who would’ve guessed that the velvet-suited, oversized tie-wearing Kanye in 2004 would become the fashion icon artist he is today?
Most iconic fashion moment: His bright red suit, complete with contrasting black tee and gold chains, lit up the stage as he performed “Runaway” in 2010. Cut to perfection and bold in just the right way (RIP pink candy-striped Oxford shirt), it established ‘Ye as one of music’s preeminent fashion leaders.
…to an unfortunate turn as a pink peacock (or something??), she eventually got to her “glam” place. Everyone loves a transformation story.
Most iconic fashion moment: Her 1998 cheetah-on-cheetahprint look is a part of Xtina’s legacy as we know it. Everything about the outfit perfectly captures 1998: knee-high black boots with a black miniskirt, lingerie-style camisole, cheetah print coat, all topped with a bold necklace. It’s one for the time capsule.
9. Lenny Kravitz has never been afraid of putting his body on full display, and for that, we thank him.
Most iconic fashion moment: It’s a close call between 1991 and 2004, but c’mon now. He’s wearing angel wings and a fringe denim vest (or is it a collar?). His abs are also basically an accessory. Nothing to say here but that this look continually leaves us feeling very blessed.
10. Britney’s fashion story is one we’re all familiar with, and it’s a saga in line with the rise and fall of her career. From teenybopper to sexpot…
But she persevered! And so did her fashion choices. Just check out that shiny, healthy hair. It was a return worth celebrating.
Most iconic fashion moment: Britney’s grand reveal of her “Oops… I Did It Again” nude, crystal-covered bodysuit from underneath her top hat and suit is practically synonymous with the VMAs now. In 2000, it was shocking. In 2014, it’s nostalgic.
Some of it good, some of it bad, but all of it memorable — save for an especially tame 2009.
Most iconic fashion moment: The VMAs were basically created FOR Madonna, and her “Like a Virgin” white tutu outfit at the inaugural show has stood the test of time as easily the most iconic fashion moment in VMA history. From the the skirt to the jewelry to the hair to her “Boy Toy” belt, everything about Madonna’s 1984 look is classic MTV.
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