Matt Damon, Dax Shepard, Ian Somerhalder (Getty, Bauer Griffin)
We're pretty sure when most guys decide to wear a fedora, they're going for more of a Justin Timberlake vibe, than say, Boy George. But if Matt Damon and Ian Somerhalder can't pull off this look without looking uber-cheesy, you my friend, probably can't either. Now if you're throwing on a hat because you're simply too lazy to do your hair, think of it this way: Girls spend hours upon hours straightening, curling, braiding...
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