Show (Air Dates): Family Matters (1989-1998)
Actor: Jaleel White

Before geek went chic, Steve Urkel was defining the socially awkward style with a combination of high-water trousers, colorful suspenders, plaid shirts buttoned to the top, natty cardigans, and oversize glasses (connected to a handy safety rope). Little did we know all of these elements would be marching down the menswear runways without a shred of irony in the late '00s. Did I do that? Yes, Steve, you did. Mad props.