Britney Spears And Justin Timberlake
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Back in 2001, Britney Spears and Justin Timberlake (the then-princess and prince of pop music) rolled up heavy to the American Music Awards. Sporting matching denim outfits and bedazzled denim accessories, Spears and Timberlake unknowingly solidified their spot in fashion horror history. They CAN be forgiven, however–they were both only 19 at the time.