The first loafer, as known and loved by men today, was reportedly inspired by a 1930s photo in “Esquire” magazine, which captured a group of Norwegian dairy farmers wearing slip-on shoes. The farmers were standing around the “loafing” area where cows were waiting to be milked, which is why in 1933 the Spaulding Leather Company of New Hampshire trademarked its new line of men’s footwear as Loafers.

A Maine shoemaker named John Bass had seen the same article, but was slower to act on it than his neighbor. So when Bass introduced his version of the loafer in 1936, he called them Weejuns, which was slang for Norwegians.

One of the characteristics of the Bass shoe was a diamond or lip-shaped notch in the decorative, supportive leather band than ran across the instep. Some say the design was suppo...sed to represent the lips of John’s wife, Alice, kissing each pair on their way out the door. But teenagers who wore the shoes started putting a penny in the slot for good luck, and the penny loafer was born.