1990s

Lisa Loeb

Lisa Loeb became America’s sweetheart when she burst onto the music scene with her song “Stay.” While she may be considered a one-hit wonder to some, her style has managed to stick around. While dressing in all black is simple you really need the tortoise shell cat eye frames to make this look work. Otherwise people might just think you’re a beatnik.

The Fresh Prince of Bel-Air

Now this is the story all about how Will Smith’s life got flipped, turned upside down. He plays a street-smart teenager in The Fresh Prince of Bel-Air, who is sent from his West Philadelphia home to live with his rich relatives in Bel-Air. He brings with him his unique sense of style, often wearing colorful prints with matching hats.

Andre Agassi

Andre Agassi has an aggressive playing style and the fashion sense to match. With everything from his dyed mullet and neon Nike apparel to his outspoken personality, he’s responsible for bringing excitement back to professional tennis in the 90’s.

Steve Urkel

Steven Q. Urkel, played by Jaleel White, lives next door to the Winslows on the TGIF show Family Matters. Urkel is the ultimate nerd with his awkward fashion, high-pitched voice, and unrequited love for Laura Winslow — at least until he drinks his cool juice and transforms into Stefan Urquelle.

Kurt Cobain

Considered by many to be the “King of Grunge Rock”, singer/songwriter/guitarist frontman of Nirvana, Kurt Cobain, became the unwillingly leader of a generation. His jaded attitude and “don’t care” appearance was something to which many kids could relate. Though his life was cut short, his music remains influential to this day.

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