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The 50 Most Stylish Celebrities of the '90s

27. Jason Lee

Why He Made The Cut: The original low-key cool guy.

There was not a nerdy white kid to be found in the mid '90s that did not want to be Jason Lee. He started as a professional skateboarder, appeared in a Sonic Youth video, and starred in multiple Kevin Smith movies. He was sharp, sarcastic and wore a mean corduroy blazer—so, he had all the 90s cool guy essentials down.

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