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Originally called "Weejuns" which is slang for Norwegian - as Norway is the country where the style originated. The penny loafer's signature leather strap with an eye-shaped slit was the perfect place to store your two cents for making calls using public phones. Hence the name-- penny loafer.
Thanks to its mix of informality and comfiness, the Weejun went on to become a staple on college campuses across the United States. The popularity of the penny loafer reached its peak in the fifties and sixties when it became synonymous with the post-war "Ivy Look" and with prep culture in general. Since then, it has maintained its association with classic, comfortable, American style.