Justin Timberlake – 2001 American Music Awards

Don’t celebrities learn anything? Just two years after David and Victoria Beckham’s leathery fiasco, another superstar couple at the time, Justin Timberlake and Britney Spears attended the 2001 Amerian Music Awards wearing a now-iconic matching denim outfit. And the result is even more cringy when you take Britney out of the picture.

Denim jacket, denim hat, denim jeans, and a denim-colored shirt? That’s too much denim if you ask us! Still, Timberlake’s all-denim look has turned into a sort of meme, one of those pop culture bits people mention again and again. Denim was supposedly very fashionable in 2001, but all trends can look ridiculous when you overplay your hand.