Will Smith ("The Fresh Prince of Bel-Air")
The Fresh Prince made us laugh, rap and wear our baseball caps all lopsided. Often with the oversized brim turned up.
Will Smith, played by, you guessed it, Will Smith, showed up on "The Fresh Prince of Bel-Air" wearing baggy pants, graffiti-print jackets and bold-colored caps, a look that became something of a uniform for cool kids who just didn't care. The kids who hung out on street corners. Or at shopping malls.
Even those oddly buttoned-up shirts looked somehow laid-back on this happy-go-lucky character who couldn't help but get on his stodgy uncle's nerves with his rapscallion ways.
And you never know -- it may simply have been the contrast with Carlton's bow ties that made Smith's style so trend-worthy. It was tough to look uncool next to Carlton.
Up next: You may know her as "L.C." …