This season marks the third collaboration between Band Of Outsiders and Sperry, and as expected the two brands didn't disappoint. The two came together and cranked out over 10 different models of the boat shoe, with the standout model being this A/O Chukka that's dressed in sweatshirt material. Rock 'em to Sunday's brunch and be the coolest guy at the table. Checks the Sperry x Band of Outsiders site to buy.