The original and the best, the penny loafer was first produced in the mid 1930's by the G. H. Bass shoe company. The Bass Weejuns Larkin are made from a leather upper, lining and sole with a rubber heel and are the quintessentially classic loafer. These were popular both the American Ivy League and the mods later on and with the right ensemble, a pair of penny loafers are hard to beat. These come in the excellent Cognac leather.