Year It First Dropped: 2008

Band of Outsiders designer Scott Sternberg made a name for himself by taking prep staples and running them through a Wes Anderson-like filter. His clothes were distinctly American, but nevertheless hip without being overly pretentious. They were also notorious for possessing an unforgiving slim fit. In 2008, neo-prep was experiencing a huge revival, and Sternberg's take on the boat shoe was a brilliantly executed footwear collaboration between an old purveyor of prep and the new popular kid. Boat shoes never went out of style, but this was the moment they became a "fashion item," and thus, worthy of paying $300 for them.