Rachel Maddow’s Converse
While we’re sorry that Ms. Maddow is the sole female on our list, we couldn’t be happier that she’s representing Converse sneakers. Though we almost lumped her in with Olbermann on the glasses train, we can’t help but notice that the stylists at MSNBC have her wearing contacts most of the time. And what better style to be known for than a pair of all around awesome sneakers. When Vogue featured the former Air American in their January 2009 issue, Maddow reportedly refused to take off her Chucks. And we love her all the more for it.