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Jennifer Lopez; 2000
I might be alone in this, but this is one of my favorite VMA outfits of all time. Maybe it's because it's just so calculated and such a hilarious effort to make Jennifer Lopez seem "real." Maybe it's because women over thirty who sport glittered mid-sections and a glorified sports bra are delightful to me. Maybe it's just that there's documentation of someone wearing a bedazzled bandana. I don't know. But this is one of my favorite VMA fashion moments of all time.