30. Luke Perry
Why He Made The Cut: He stole our childhood crush's heart, so we stole his style.
A then modern-day (albeit factory-made) James Dean, Luke Perry's loner rebel attitude on "90210" was the teen-hearthrob-magazine thing of legend. A wardrobe rife with Wayfarer shades, ripped jeans and motorcycle boots naturally went hand in hand; although, the whole not-looking-40-while-playing-an-18-year-old thing proved to be a slight side effect.