44. James Wilson

Occupation: Blogger, Secret Forts

There are certain guys that just live it. This applies to bloggers as well. James Wilson's influential digital presence, Secret Forts, is only surpassed by his actual one. This stylish jack of all trades leads the way for his fans and imitators alike. We wouldn't sum up James' look as simply "Americana" — that would only tell half the story. Dude can rock a pair of J's as easily as he rocks a pair of Red Wings, or whatever boots are going to be all the rage six months from now.