Britney Spears

Matching denim with Justin Timberlake, American Music Awards, January 2001 Spears arrived in a strapless patchwork denim gown beside Timberlake in a full denim suit and hat, and the photograph became shorthand for the whole era. Spears herself later called the outfits tacky in her memoir, which is a fair verdict on the matching. The useful lesson for now is the gown on its own: a patchwork denim maxi skirt or dress looks deliberate today, while head-to-toe denim on two people still reads as a costume.