1. Will Smith
Show (Air Dates): The Fresh Prince of Bel-Air (1990-1996)
Actor: Will Smith
Would we repeat any of Will Smith's Fresh Prince get-ups today? Hell no. But we're more than happy to swim in that early '90s nostalgia every time we catch a rerun, thanks to Smith's healthy collection of so-bad-they're-good technicolor wind-suits, baggy neon tanks worn with matching shorts, flashy high-tops, caps worn flipped up and to the side, and a myriad of old-school hairstyles. Oddly enough, with the crazy pants trend currently ruling women's runways, cringe-worthy Fresh Prince style is still very much alive—for better or for worse.