The History of the Penny Loafer

Posted on September 24 2020

The History of the Penny Loafer

Likely the first pair of dress shoes that you owned as a child, the penny loafer is akin to a pair of khakis or a polo shirt - it has transcended seasonal trends and is regarded as a timeless essential. 

Perhaps it is the versatility of the penny loafer that has resulted in its unshakeable popularity throughout the years. After all, it can be argued that no other shoe style can offer as many styling possibilities: the penny loafer can elevate the most laidback looks while also being the perfect finishing touch to smart casual ones - equally at home whether paired with tapered trousers or linen shorts. 

From the penny loafer’s international beginnings to how it became synonymous with Ivy League style, let’s take a quick look at its rich and varied journey as well as what makes the Jay Butler penny loafer unique - here at Jay Butler, we’re all about loafers that are well-made, well-styled, and well-priced. 


How It All Began

In the early 1900s, a Norwegian man named Nils Tveranger wanted to improve the design of the teser, a traditional laceless shoe that was worn by local fishermen and peasants. The teser was a tough yet lightweight slip-on style that was made from leather. After going to America to study the art of cordwaining, he created the Aurland moccasin when he returned to Norway, which combined elements from the teser and the Iroquois Native Americans’ moccasins. 

The Aurland moccasin was discovered by European and American foreigners around the time of the interwar period. Enticed by rumors of exceptional salmon fishing and mountaineering, they began to visit the Valley of Aurland in Bergen and took note of the comfortable-looking footwear that local fishermen wore. They marveled at the simplicity of the shoe and took home a pair or two as souvenirs. 

These foreigners — wealthy sportsmen and the well-traveled elite — wore the Aurland shoes back home in fashionable places like Palm Beach, where an Esquire magazine staffer spotted the first pair in 1935. According to Esquire, the Aurland shoes were usually paired with light-colored suits and a Panama hat or a fedora.


From a Norwegian Local to an American Icon

Arnold Gigrich, the founder of Esquire, saw the potential of the Aurland moccasin and decided to partner with a distributor to bring a sample to John Bass, the son of the founder of American footwear label G.H. Bass. By 1936 the label had adapted the Aurland into the Weejun: a thicker-soled adaptation with a distinctive cutout in the middle of the strap. 

The Weejun—an American take on the word “Norwegian”—was advertised as Norwegian fishing shoes and first retailed for $6.50. An early advertisement refers to the penny loafer’s versatility: “Not shoes, not slippers, not moccasins, they are ideal for the beach, a camping trip, or lounging about the locker room or house. Fine for informal occasions.” A later advertisement aptly calls the penny loafer the “Symbol of Elegant Leisure.” Penny loafers became an instant hit, so much so that women even began buying them for themselves and brands around the country began producing their take on the style.

The Penny Loafer Hits the Ivy League

Lured by the well-priced penny loafer’s convenient laceless design that was ideal for rushing to class in the mornings, it became the ubiquitous shoe for American schools and college campuses from the 1940s to the late 1960s. Worn by students year-round and paired with everything from shorts to tweed separates, the term “penny loafer” was widely used as the go-to nickname after the method of putting a coin in the strap’s slot became the popular norm. Wearing the penny loafer sockless also became a cool trend at the time, though it is widely debated whether this was due to John F. Kennedy’s influence or the lazy nature of students.

The penny loafer’s place in college campuses was cemented in 1960, when a student newspaper at the University of North Carolina published an editorial with the subheading stating that the penny loafers were “the thing on the feet of those who are with it.”

The Penny Loafer: From Jazz Musicians to Wall Street Bankers

The Ivy Style wasn’t just exclusive to college students; it was also adapted by working class GIs and jazz musicians like Miles Davis up to the late 1960s. Davis was regularly seen in the classic Ivy League uniform of the Oxford shirt, khaki chinos, and penny loafers. Other iconic figures of the time such as James Dean regularly wore penny loafers with blue jeans and a white tee, while Elvis Presley was often seen in them including in 1957's Jailhouse Rock.  

From the 1980s onwards, penny loafers were worn with suits by Wall Street bankers and paired with jeans on weekends. Even punks were no strangers to them, styling their beat-up loafers with ripped denim and leather jackets, proving that the iconic shoe style was adopted by various cultural groups.

Jay Butler’s Cromwell Loafer

The penny loafer remains a popular and trusted go-to with unparalleled versatility, whether paired with tapered trousers or linen shorts. Here at Jay Butler, we’re all about loafers that are well-made, well-styled, and well-priced. 

Our Cromwell Penny Loafer is the ideal loafer: casual and refined with a shortened vamp, a subtle beefroll, and a streamlined leather sole that requires minimal break-in while still having the durability to last for years. Rendered in an extensive selection of hues and materials, there’s a Cromwell to suit every style and personality. Want a style that will let you stand out from the crowd? Opt for the Cromwell in American alligator. Looking for something for the warmer seasons? The Cromwell in perforated leather is the perfect choice. 


The best part about our Cromwell Loafer? Pair it with pretty much anything in your closet and you’re good to go. Want to look sharp on a hot summer day? Go for our Cromwell in navy or dark brown suede to spruce up a pair of shorts and a linen button-down. For a more formal setting, you can’t go wrong with pairing our dark brown full-grain leather Cromwell with a navy suit or blazer. 


Shop our Cromwell Penny Loafer here.

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  • Chuck Pfeifer : March 12, 2023

    I have been wearing loafers for decades. They are modeled after the Oldmaine Trotters loafers of the fifties with flat strapped penny holders and hand sewn vamps and kickers. They are extremely soft and comfortable!

  • Chuck Pfeifer : March 12, 2023

    I wear only penny loafers. However, as a man, I wear only women’s penny loafers made to my size 101/2C. They are modeled after the legendary Oldmaine Trotters with their hand sewn vamps and kickers. The leather is glove soft and are very sexy..I find men’s loafers are too large and “clunky” while women’s loafers are slimmer and softer. I have all my loafers custom made in Maine and own 30 pairs in different colors.

  • Envie Escaso: March 12, 2023

    Very good write-up. I certainly love this website. Thanks!

  • Paul R.: March 12, 2023

    “… lounging about the locker room …”

    Was this ever a thing?

  • Rhoden Jones: October 13, 2020

    Great loafers, the penny loafers goes with every occasion

  • Jack J Virzi: September 28, 2020

    Send me magazines and booklets Of your fall and winter Clothing and shoes and boots

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