16. Converse Jack Purcell
Things you probably didn't know about the Jack Purcell: It was designed by a Canadian, who played badminton, and has been produced under two brand names. Originally designed for the B.F. Goodrich Company, the Purcell (named for John Edward Purcell) became part of the Converse family in the '70s. The signature smile on the toe is the shoe's hallmark, a cheeky statement of individuality which speaks to a quiet truth: The Purcell is the thinking man's Chuck Taylor. The model inspired advertising campaigns that gave handsome rogues at country clubs nation wide courage to talk to cougars. And, it helped define prep style (just flip through the pages of Take Ivy for evidence).