Team: New England Patriots
Dresses like: Privileged teenager x Austrian tourist

Because he has a fistful of rings, a $30M contract, and goes home to Gisele Bundchen, Tom Brady's confidence has reached an almost irresponsible tipping point. At this rate, dude's six months away from walking his kids to the park in nothing but Richard Simmons-style dolphin shorts and his shoulder-length hair in cornrows. He also cosigns Uggs, which is strange because the Patriots quarterback doesn't need to endorse anything besides bubble screens. Like, Tony Siragusa hawks adult diapers because he lost his fortune mainlining pie filling. But between Tom and Gisele, the Brady family pulls more bread than the Pillsbury Doughboy on a dry spell, so endorsing the walk of shame's official footwear has to be a passion project.