The penny loafer originated in the 1930s when loafers of several varieties were fashionable as men’s and women’s shoes. Somewhat unbelievably, this fashion started with the Spaulding company when they produced shoes styled after those of Norwegian dairy farmers that had appeared in an article in Esquire Magazine. However, it wasn’t until a few years later that the penny entered the equation.
In trying to add his own unique stamp to the popular loafer, John Bass began producing loafers he called Weejuns that had a strap across the top of the shoe for style purposes, as a loafer is traditionally defined by having no buckles or laces. This strap had a split design that was supposed to look like a pair of lips. This opening in the strap was soon used as a way to add a decorative touch to the usually simple loafer and small objects, such as pennies, were often placed there. A stylistic embellishment that had once been peculiar to Bass’s shoes became synonymous with an entire fashion.
When pay-phones were still ubiquitous and hadn’t yet been raised to a quarter, the penny loafer was often the source of funds for an emergency phone call home, especially for school-age children or teens on dates.
Penny loafers have been unique since their inception in that they have moved between both form and casual fashion and men’s and women’s fashion. Acceptable for both genders and viable with everything from a suit to jeans and even shorts, penny loafers have long made a smooth transition from work to play. The unique style of the vamp of the shoe that gives them their name has even been transplanted onto a high-heeled (and therefor non-loafer) version for women.
For men, the penny loafer has generally been worn without socks since the 1960s. This style was particularly popular then, and in the 1980s, where the penny loafer with a suit but no socks was emblematic of preppy fashion. It was seen commonly on style-leading celebrites of the time, such as Don Johnson of Miami Vice.
Women more commonly have worn their loafer with socks or stockings, but as bare legs, even with skirts, have become more acceptable for women, their loafers have also become fashionable as a sock-free shoe, at least in casual circumstances.
Despite its presence in many fads, the penny loafer is a simple, classic and understated shoe with practical, long-term fashion value.