Year Released: 1983

Over a storied 64 year period, the other Dassler brother has hitched its fortunes to a crazy array of historically significant athletes: Jesse Owens, Pele, Jay Piccola, Tommy Smith, Diego Maradona, Clyde Frazier and now Usain Bolt. Whether by design or by chance, most of these icons are as famous for what they stood for off the court as on it. Guillermo Vilas was no exception. Off the court, Vilas stood for suntan lotion and royal tail. In 1982, he straight up skipped Wimbledon to do the damn thing with Princess Caroline of Monaco on an "undisclosed island" (Maui) for a week. My man Guillermo. The G Vilas launched in 1983. It was a tank on a giant PU bottom. Here is why the G Vilas matters. Of the 50 shoes on this list, there are three that have been commercially successful from launch to right this minute. The G Vilas (now called the GV Special) is one of them. In some areas of Philly people call them Luttermans. In other areas, people call them Sweetings. I was at the DMV in Philly for six hours last week, and I must have seen 25 pairs on feet.