The history of the Penny Loafer is a bit muddled these days, but legend has it that in the 1930’s, Norwegian fisherman were wearing moccasin-style slippers for comfort. The country also began exporting them to the rest of Europe. Americans visiting Europe at the time would bring them home, but it wasn’t until Esquire magazine featured them that these leisure slip-ons became known to the masses in the United States.