The penny loafer may epitomize preppy New England style — after all, John F. Kennedy wore penny loafers on the golf course. And John Cheever, chronicler of New England preppy angst, was known for his wrinkled khakis, blue-and-white striped Brooks Brothers shirt and Size 6 penny loafers.
But the penny loafer didn’t originate in New England.
Nonetheless, New England played an important role in the development of the penny loafer, in large part because of its long shoemaking tradition.
New England as Shoe Capital
The region’s indigenous people made moccasins by hand for centuries. They also provided the design inspiration for the penny loafer (more about that in a bit). Nine years after the Pilgrims landed, a cordwainer arrived to make shoes for the colonists.
Shoemaking then grew as a cottage industry in New England. Farmers, like John Adams’ father, often made shoes as a side hustle. Full-time cordwainers made shoes at home or in small workshops called ten-footers that dotted New England towns. Randolph, Brockton, Brookfield, Lynn and, later, Natick became early centers of the shoe industry in Massachusetts.
Eventually, demand for shoes grew. Employers introduced sewing machines and centralized production in factories. By 1850, Lynn alone produced 4.5 million shoes a year, and Massachusetts had 50,000 journeymen shoe workers.
The transition to factory work did not go smoothly. On Washington’s Birthday in 1860, some 20,000 shoemakers went on strike in 25 New England shoe towns. New England shoemakers strike of 1860 resulted in wage hikes for men and some union recognition.
The Teser, Precursor to the Penny Loafer
The penny loafer has other roots in the fjords of Norway. Norwegian peasants traditionally wore a slip-on shoe called a teser. In a small western Norwegian town called Aurland, they were popular among fishermen and farmers.
Sometime in the 1890s an Aurlander named Nils Tveranger decided to go into cordwaining. He went to the obvious place for an apprenticeship: Boston. There he met the indigenous moccasin, which inspired him to design the loafer. It’s the gathered toe stitch that marks the Native American influence on the penny loafer.
Tveranger then returned to Aurland and started making shoes. Eventually, 13 shoe factories grew up in the tiny town.
Aurland happens to have world-class salmon fishing, which attracted upper-class American and English sportsmen between World War I and World War II. They admired Tveranger’s slip-on footwear, and started bringing them back to England.
It wasn’t a penny loafer yet, though.
Birth of the Penny Loafer
The Aurland shoe migrated to Europe’s upper-crust neighborhoods and stylish American watering holes. Eventually a sharp-eyed reporter for a new men’s magazine called Esquire noticed the Aurland shoe. It isn’t clear where he spotted the shoe; according to one version, he saw it in Palm Beach. According to another, he spotted it in the European cafes of the Lost Generation. Maybe both. Whatever the case, representatives from Esquire and from a tony New York men’s store, Rogers, Peet, met with John Bass, president of G.H. Bass, a Wilton, Maine, bootmaker.
They tried to persuade him to make the . Bass didn’t think the Norwegian peasant shoe it would sell. He later said, “I didn’t think this type would go over, for it looked like a house slipper to be worn outdoors.”
Bass, however, succumbed, and went along with the Esquire and Rogers, Peet people. The company added the strip across the upper with the slot for the penny.
Bass called the shoe Bass Weejuns (for Nor-weejun). The loafer ended up a huge hit among the leisure class. Then after World War II it migrated to college campuses in a big way, where it joined khaki pants and blue blazer in the preppy pantheon of style.
However, the penny loafer went beyond New England, both in the manufacture and in the wearing. Such nonpreppies as James Dean, Elvis Presley, David Hockney and Elton John wore penny loafers (the latter chose a two-toned version from Prada).
The Penny Loafer Gets the Penny
No one knows for sure how or why people started putting coins in their footwear. Some say they did it so they’d always have change for the pay phone. Eventually the copper penny became more aesthetically acceptable than the silver nickel or dime. Or maybe it was just a luck thing.
Today, the penny would prove problematic for air travelers, as it might alarm the magnetometer at security. Plus, pay phones don’t exist anymore.
In 1998, Bass stopped making Weejuns or any other kind of shoe in the United States after 122 years. Bass’s parent company, Phillips-Van Heusen Corp., shut down the Maine factory and sent 350 jobs to Puerto Rico and the Dominican Republic.
You can still buy penny loafers from the fjords of Norway. Aurlands shoe company sells a line of them for an average of $400 a pair. But they’ll ship for free.
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Images: Images: Aurland mountain and fjords By Aconcagua – Own work, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=1020902. Penny loafer by Robert Sheie via Flickr CC By 2.0