Hilary Duff, 2005
Hilary Duff has been a red-carpet regular since she was 13 when she won hearts on Disney's "Lizzie McGuire." Slowly but surely, her style transformed from girly to glam. Nowhere was her fashion evolution more evident than at the 2004 VMAs.
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Hilary Duff looked like a dream in her sequins and fringe dress as she channeled the uber-chic, high-fashion flapper within. Duff was dating Joel Madden from Good Charlotte then, and this was the first time the couple appeared in public together and presented an award onstage.
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Lady Gaga, 2009
What can one say about Lady Gaga that hasn't already been said? Over the years, the trailblazing star has worn nearly every outlandish look imaginable and made it work. Still, who can forget her fabulous black ensemble at the 2009 VMAs?
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The star wore a black lace Jean Paul Gaultier dress with a Dragon print silk underlay from Gaultier's fall/winter collection. Gaga completed the look with a neck brace and mask by Keko Hainswheeler. She was also accompanied by Kermit the Frog.