Popular penny loafers from the 1960s

Updated July 20, 2017

One of the most popular shoe styles for both boys and girls during the 1960s was the penny loafer. These versatile shoes were easy to slip on and comfortable for everyday wear. It was hip to put a penny in the little slot on the top of the shoe, and if you were practical, you could use a dime instead, the cost of a call from a pay phone at the time. Bass Weejuns and Sebago were the most popular brands.

History of the Penny Loafer

The first penny loafers were the Bass Weejuns, introduced by the shoemaker G.H. Bass & Co. in 1936 and based on a men's shoe worn by Norwegian farmers. Sebago created a similar shoe in the 1940s, styled after Indian moccasins. By the 1950s and 60s, penny loafers had become a symbol of "cool," spotted on celebrities like Miles Davis, Steve McQueen and President John F. Kennedy. Constructed of heavy black, brown and mahogany leather, with no laces or buckles, these loafers were designed with a strap across the top in the shape of a pair of lips. Soon, wearers were using this decorative feature to carry a small object, most often a penny. By the 1960s, the penny loafer was synonymous with casual fashion, a look that could be dressed up or down and worn by both men and women.

For Boys and Men

During the 1960s, penny loafers were almost ubiquitous on the campuses of prep schools and Ivy League colleges. Older boys and young men wore them with khaki trousers, shorts, a tennis sweater or even a casual suit for a preppy "young American" look. About this time it also became a fashion statement to wear the loafers without socks, even in cold weather, or with slacks and a sport coat. This trend continued into the 1980s and is still considered a classic look today. Penny loafers also lent themselves to a more rebellious, James Dean-inspired effect, when worn with jeans or tight-fitting chinos, white socks and a white T-shirt.

For Girls and Women

Teenage girls in the 1960s often wore penny loafers with skirts and matching knee socks. Their older sisters were more likely to wear them with pantyhose or even bare legs, with either skirts or slacks. During that era, girls were still not allowed to wear trousers on most campuses, however, but wore kilts with button-down oxford cloth shirts and crew-necked cardigans instead. Unlike men, women would change to more formal footwear for dinner parties or other occasions, but might switch back to their Weejuns when they donned madras Bermuda shorts later on.

An Enduring Fashion

Penny loafers remain a popular shoe style today, with Bass and Sebago still producing them in their classic form for a loyal customer base. Other shoe manufacturers have got into the act, offering penny loafers in a variety of colours and materials, include suede and patent leather. It seems that nostalgia, comfort and style have combined to make penny loafers an enduring footwear fashion.

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About the Author

Alice North has been writing professionally since 1980. She currently writes for "Congressional Digest" and "International Debates." She has written for politicians, associations, think tanks and event production companies, among others. Her work includes speeches, articles, newsletters and scripts. She attended the Boston Conservatory of Music and New York University.