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The Most Daring MTV VMA Fashion Of All Time

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September 12, 2009 - Michael Loccisano/Getty Images North America more pics like this »
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18. Jennifer Lopez 2009
Jennifer Lopez makes another appearance on our list with this Louis Vuitton look at the 2009 show. The beige mini dress featured a cold-shoulder design with long velvet sleeves, crossover straps, and a deep sweetheart neckline that showed off her décolletage.

JLo finished off her attire with mesh peep-toe booties by Christian Louboutin along with a black leather clutch. Her hair was styled in a tight slicked-back updo, which she teamed with a pair of dangling earrings. She certainly has a knack for choosing the most uncommon looks!