More of the Most Daring MTV VMA Fashion Looks of All Tim

Jennifer Lopez, 2001

Jennifer Lopez wore a one-piece, high boots, and a sun hat to make this a head-turning look at the 2001 MTV Video Music Awards. Unlike her all-out glam looks from the previous years, the queen kept it relatively understated but still risqué in a breezy mini Cavalli.

 

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She still manages to stand out on the red carpet. When you’re JLo, you cannot blend into the background, even if you try.

Kelly Osbourne, 2002

The Osbourne star played into the graphic tee trend of the 2000s with a top that read: "My Boyfriend Is Out of Town." She also rocked a crimped bob, yellow eyeshadow to match her tee, and red lips to go with her shirt again. Now if that doesn’t scream wild child, we don’t know what does!

 

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But there's much more to Kelly Osbourne, as everyone knows. She is a triple-threat entertainer — singer, model, and fashion designer. Apart from her edgy fashion sense, Osbourne is also known for her thought-provoking debates on talk shows and reality television.