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Ashton Kutcher

Ashton Kutcher's rebellious style can be questionable, but the suit, beanie and beard combo he was sporting at the GQ Gentlemen's Ball recently struck the perfect balance between polished and povo.

It's a look that's not hard to recreate, but attention to detail is key to avoid the homeless man subtext. Note the well tailored suit, matching belt and shoes and statement watch peeping from his jacket sleeve - all teamed with just the right amount of scruff. Owning it.