adidas Robert Haillet
Current Price: $100
If you're thinking these look an awful lot like Stan Smiths, you're right — the all-leather tennis shoe began as a signature shoe for the lesser-known Haillet before adi smartly re-designated them the Stan Smith. Haillet didn't win much of anything in his career; Smith won the '71 U.S. Open, '72 Wimbledon, and was inducted into the Tennis Hall of Fame in '87. Still, these are a unique piece of adidas arcana for just a C-note.