The History of Penny Loafers

In the 1930s, payphones cost two cents. In response, the loafer was redesigned to allow just enough space to place a penny in each shoe, ensuring that the wearer would have enough money for an emergency phone call. This is how the penny loafer was born. The penny loafer had its heyday in the late 1950s and early 1960s. Despite the fact that payphone costs had risen to ten cents, the penny loafer became a key part of Ivy League style in the postwar period. (Some young gentlemen put dimes in their shoes instead of pennies, while others, in true preppy fashion, continued to use pennies out of a sense of tradition.) While penny loafers no longer serve a practical purpose, the shoes have become an American classic. They are still sometimes worn to the office and remain a hallmark of preppy style to this day.