Few items in the preppy wardrobe carry as much quiet authority as the penny loafer. Simple, sturdy, and endlessly versatile, it’s the shoe that manages to look just as natural shuffling across a college quad as it does paired with a summer suit at a cocktail party. Like all good preppy staples, its history is equal parts tradition, reinvention, and a touch of Ivy League ingenuity. As with any origin story that goes way back some details may be a bit unclear or up for discussion. But generally this is most likely how it came to life and got its name. 

The first penny loafers were of course not the modern take, and they weren't called penny loafers at the time. It is generally agreed that the origin story of the penny loafer starts with Nils Tveranger. Some time around 1890, Nils left Aurland in Norway to go overseas to Boston where he learned and perfected shoe making. But he only stayed a few years and soon went back to his home country. While in the US, he had been inspired by the Native Americans culture. As he started producing his own shoes, he combined the design of Native American moccasins and local shoes called tesser. Nils called them the Aurland Moccasins they became wildly popular among local fishermen and across Europe. 

About 30 years later, it was popular among wealthy Americans to travel across Europe. Some of those travelers fell in love with the Aurland Moccasins and brought them back to the US. 

Enter George Henry Bass, founder of the American shoemaker G.H. Bass and the man to bring the penny loafer to the market. But he wasn’t in love at first sight. Apparently he thought it looked like a house slipper worn outside. But eventually he came around and launched his version in 1936. Bass added a thicker sole along with the iconic strap with cutout right above the toes.

He called them the Weejuns. The name might sound a bit weird at first but it’s derived from its history. Norwegians simply became Weejuns.

So how did it go from Weejuns to Penny Loafer? The Weejuns became very popular among students across the Ivy League, they were worn year around with all sorts of outfits. The strap above the toes along with the cutout made for a perfect place to store a dime or a penny when calling home. This became a trend, signaling that you had real Weejuns from GH Bass. While you can still Weejuns at GH Bass, the shoe style is now worldwide known as the Penny Loafer thanks to those College kids calling home. 

Today, the penny loafer is more than just a shoe, it’s a shorthand for an entire lifestyle. Slip them on and you’re stepping into a tradition that stretches from Norwegian craftsmen to Ivy League quads, from smoky jazz clubs to seaside summer houses. They’re proof that true preppy style isn’t about chasing trends but about embracing pieces that endure, adapt, and quietly signal good taste. The penny loafer has walked that line for over a century, and it shows no signs of slowing down.