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Steve Urkel (Jaleel White), Family Matters
Those flood pants. And kaleidoscopic cardigans. And rolled-up jeans. And suspenders. And thick-rimmed glasses. Urkel was nerd personified in the '90s and he owned it. Well, except for that time he became the ultra-suave Stefan Urquelle. The ironic thing is that while we laughed at Urkel's nerdy style back in the day, it's considered hipster chic now. No wonder New Girl's Jess is into him! Did he do that?