There's a slot in the strap of a penny loafer. If you've ever wondered what it's actually for — you're in good company.
The answer is simpler than most people expect. Penny loafers are called that because people used to put pennies in them. A real coin, slipped into the strap's small cutout, carried there through the school day or the walk across campus.
Here's where that habit came from, why it stuck, and what it says about one of the most enduring shoe silhouettes ever made.
It Starts With a Norwegian Farm Shoe
Before the penny, there was the loafer. And before the American loafer, there was a Norwegian farm shoe.
In the early 20th century, Norwegian farmers wore a simple slip-on shoe — no laces, no fasteners, just a sturdy moccasin-style construction easy enough to get on and off between work and home. That silhouette made its way across the Atlantic, and in 1934 a shoe company in Maine called G.H. Bass & Co. introduced their version: the Weejun. The name was a truncation of "Norwegian." The shoe had a low-cut toe, a clean upper, and a decorative leather strap across the vamp with a small diamond-shaped cutout in the center.
That slot was ornamental. Nothing more. A design detail that gave the strap some visual interest.
Then American teenagers got hold of it.
Why People Started Putting Pennies In
By the 1950s, the Weejun had become standard-issue footwear among prep school and Ivy League students in the American Northeast — worn with chinos, Oxford shirts, and the studied casualness of people who considered sneakers too informal. At some point during that decade, students started sliding pennies into the strap's cutout.
There are three explanations that get passed around:
The payphone theory. A local call cost one cent in the early part of the 20th century. Keeping a penny in your shoe meant you always had emergency phone money on you — practical, if you discount the inconvenience of digging it out.
The good luck theory. Carrying a penny was considered lucky. Putting one in your shoe was considered especially lucky — a superstition that predates the loafer by centuries and has versions in cultures across Europe and North America.
The style theory. Someone did it, it looked interesting, and other people copied it. Which is how most fashion traditions actually start.
The payphone story gets repeated most often, though the timing is slightly off — payphone prices had already risen above a penny before the habit peaked in the late 1950s. The truth is probably all three reasons layered on top of each other: it was practical enough, it looked distinctive, and it became a small marker of belonging in a subculture with very specific dress codes.
When "Penny Loafer" Became the Name
By the late 1950s and into the 1960s, "penny loafer" had settled into common American usage. The Weejun name faded from casual conversation. People didn't ask for a Weejun anymore — they asked for penny loafers, defined now by the coin rather than the country of origin.
The habit of inserting actual pennies faded faster than the name. But the slot stayed. The silhouette stayed. And the name — which had never been official, just organic — became permanent.
What Happened to the Silhouette After That
The penny loafer went from collegiate staple to American mainstream to global fashion reference. It appeared in every major preppy revival — the 1980s version, the 1990s version, the current quiet-luxury cycle. Designers moved the slot, changed the strap, added metal hardware. Some versions dropped the cutout entirely and kept the shape.
The basic proposition turned out to be nearly perfect: a clean, unstructured slip-on with a horizontal detail across the upper. Simple enough to be versatile, structured enough to look intentional. Every decade has found a reason to keep it around.
What This Has to Do With Raffia
The classic penny loafer is a leather shoe. But the silhouette translates across materials — and in warm weather, leather is often the wrong answer.
Our men's raffia loafers carry the same low vamp, the same slip-on construction, the same clean lines — built from natural Moroccan raffia instead of leather. Lighter, more breathable, and better suited to the months when a leather shoe becomes more of a burden than a choice.
The women's raffia loafers work the same way: the silhouette is faithful to the classic shape, the material is natural and handwoven. Raffia isn't processed through a factory — it's woven by craftspeople in Marrakech who understand how the fiber behaves under tension, where it flexes, and how to shape it so it holds. If you want to understand that process, our post on how raffia shoes are made goes into the detail.
The connection to the penny loafer tradition isn't just visual. The original Weejun was made to be worn, not displayed — a practical shoe that happened to look good. Our raffia collection runs on the same logic. Handmade to be used. Read our story if you want to know where the brand started.
The Short Answer
Penny loafers got their name because American students in the 1950s slipped coins into the decorative cutout in the strap. The habit had practical roots, spread as a style marker, and gave the shoe its permanent name — even after most people stopped carrying the coin.
The slot is still there. The name stayed. The silhouette has outlasted every decade that tried to replace it.
If you want to wear the shape in something lighter than leather, the raffia loafer is where to start. Same silhouette. No penny required.