Put Some Prep in Your Step with a Pair of Penny Loafers

Burgundy penny loafers
Image credit: Laura Thonne on Unsplash

The 1930s in the United States saw the emergence of a new type of shoe that would quickly snowball into becoming a quintessentially American style. Its origins, however, can be traced somewhat further afield.

Penny loafers — that adaptable staple of American preps, punks, and even the occasional president — were officially invented (and are still sold prolifically by) G.H. Bass & Co. The direct predecessor of the penny loafer, however, can be traced back to a Norwegian shoemaker named Nils Gregoriusson Tveranger, who created a shoe design known as the Aurland moccasin. In its creation, Tveranger likely drew both on the traditional Scandinavian fishermen’s shoes of his local surrounds and the moccasins worn by the Iroquois tribe, which he had discovered in his adolescent years as an apprentice shoemaker working in America. Aurland mocs soon spread throughout Europe and soon made their way back across the Atlantic on the soles of urbane globetrotters vacationing in Europe. A similar style was duly introduced stateside by the New Hampshire-based company Spaulding, who dubbed their soft, slip-on moc-style shoes ‘loafers’. So when G.H. Bass & Co (who were located over the state border in Wilton, Maine) added their own moc toe slip-on into the mix, they decided to call it the ‘Weejun loafer’, partly as an American corruption of ‘Norwegian’ and partly to taxonomise it as part of this newly-created style of footwear.

The Bass Weejun was, however, a beast entirely unto itself. It featured a sturdier sole, a dressier aesthetic, and — most importantly of all — a slotted saddle which fortuitously proved to be the perfect size for housing some stray pieces of change. As a result, whether for practicality, superstition, or simple affectation, college students started carrying pennies around in the slots of their loafers — ideal (so the story goes, anyway) for making a phone call in a pinch back in the days before mobile phones and higher call charges. Hence the numismatic nickname ‘penny loafer’.

By the 1950s and ’60s, these penny-pinching collegiate types had turned their trusty loafers into a cultural phenomenon. Their affordability and slip-on convenience meant Weejuns were ideally suited to campus life. What’s more is that the dressing habits of these early adopters still define many of the ways we still wear penny loafers today. For instance, whether in the Ivy Leagues or otherwise, one thing nearly all college students have in common is a degree of scruffiness. They might, for instance, decide to wear their leather loafers with gym socks. Or, if they happen to be running late for class, pull them on without any socks on at all. And, since they’re already desperate enough to be stowing spare pennies in their shoes, they aren’t necessarily flush enough to replace said shoes once they start falling apart. Hence the stories of early preps simply wrapping their Weejuns in duct-tape before hitting the pavement again. Fast forward a few decades and we’re still perennially wearing Weejuns with white socks or no socks at all while walking them through several sets of soles and championing a certain pavement-worn patina.

Elvis Presley wearing penny loafers
The blue suede shoes get a lot of airtime, but the King also loved penny loafers
Image credit: Tullio Saba / Public domain

The penny loafer may forever be associated primarily with New England preps, but from the mid-twentieth century onwards it found a place in the wardrobes of everyone from working-class GIs to jazzmen to Wall Street bankers. Some of its more notable fans include style luminaries like James Dean, Paul Newman, Elvis Presley, Chet Baker, Miles Davis, Audrey Hepburn, Grace Kelly, President John F. Kennedy, and Michael Jackson, whose high water trousers, white socks, and glossy loafers served to highlight some equally eye-catching footwork.

It’s worth pointing out that the Weejun-style penny loafer is, of course, far from being the only game in town. Penny loafers are made by just about every self-respecting purveyor of leather footwear (animal or otherwise) and run the gamut in terms of formality, ranging from rounder, chunkier models on the casual side up to sleeker numbers made with fine leather and minimalist stitching on the more formal end. They also come in the many shades of browns and black you would expect to find with any leather shoe, but penny loafers also enjoy the somewhat more unique distinction of working well in two-tone colourways and in burgundy (the latter being perhaps the most classic choice of the Bass Weejun).

In many ways, one could argue that the penny loafer is an ideal shoe. It’s versatile enough to be worn with smart trousers to the office and jeans and shorts at the weekend. It tends to be very comfortable (if properly sized and worn in), it can be surprisingly affordable (a pair of Weejuns goes for about £150 or less), and often has an appealing air of buoyant youthfulness that is rarely captured in footwear at the more formal end of the spectrum. This might be the reason why penny loafers have found a natural home in the streetwear of recent years and seemed to take off again in a big way in the wake of the dreariest days of COVID-19.

I bought a few pairs myself during the pandemic and now wear them out every chance I get, which, given Scotland’s climate, is admittedly less often than I would like. Whenever I do get to wear them, though, I always feel like a million bucks, which seems like good value for money from a pair of shoes famed for carting around pennies.