When Sperry and Band of Outsiders team up, you know you're getting a quality product. The Sperry Topsider x Band of Outsider Penny Loafer is essentially a laceless, fancified version of the Authentic Original. However, this time around, the hand-sewn shoes are unlined and unconstructed for barefoot comfort and all day wearability. $195
[Sperry Topsider]