From PEOPLE Magazine Click to enlarge
The collegiate-looking cutie-pie has graduated to the sharp style of Armani.

Sure, the onetime model can make any old suit look okay, but in Tom Ford at the 2003 MTV Movie Awards with P. Diddy, the pair's gleaming gangsta glam nearly stole the show.

This team jersey? Its days may be numbered.

No kids' stuff at the Teen Choice Awards: Kutcher looked suavely hip.

Hats off to Mr. Diddy: We didn't think anyone could get the former Iowa farm boy out of his trucker caps and into fedoras.

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