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1
The 50 Most Stylish Celebrities of the '90s

3. Will Smith

Why He Made The Cut: He was fresh before he was Big Willie.

Being the Fresh Prince alone would've been enough to lock Will Smith in a spot on the list. But more than just an insane collection of Air Jordans early on, Will made the nearly impossible (and seamless) transition into sleek, mature red-carpet styles. Coincidentally, his blockbuster status wasn't far behind.

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