Usher has really improved his style lately, but it's not like the singer's style emerged overnight. It takes time (and risks) to fall into your own look, and the '90s served as a sartorial schoolyard for the enduring star.

Usher was fresh in his younger years (rocking cool sportswear), but his best style moment came in 1997's "Nice & Slow" video, as he rocked a handful of outfits that were all notable: leather jackets, bright print shirts, and even an eyepatch à la Slick Rick—with a fur coat to match.