Cole Haan, currently celebrating is 80th anniversary, is updating the American classic with the Air Barrett. Sounding more like a pair of Nikes than a pair of penny loafers, it has that particular name for a reason. The shoe is a marriage of hand-finished leather and discreetly placed Nike Air technology inside a hybrid heel. With the Air Barrett, Cole Haan has managed to put a modern twist on the penny loafer largely due to its innovation in shoe technology.  [$195.00 at Cole Haan]