From Ivy League campuses to the silver screen, from rural New England to the big city, the penny loafer is a quintessential American sartorial staple.
Simple in design and construction, this iconic piece of footwear is still produced by hand by G.H. Bass, the American company that began popularizing the style in 1936. And while it may no longer be a quintessential piece of Ivy League kit, its no-fuss, versatile silhouette is still a go-to choice for stylish gentlemen everywhere.
A Norwegian bridegroom wearing slip-on on shoes, the inspiration for the American penny loafer (Image by Port Magazine)
While the precise origins of the penny loafer are somewhat murky, the story goes something like this: In 1891, a Norwegian named Nils Tveranger from the village of Aurland left his home for Boston, where he studied shoemaking. Returning to Norway in 1894, he began producing shoes inspired by Native American moccasins he had seen in the United States as well as by a local slip-on called the tesser, which was popular with local fisherman.
Wealthy Americans traveling abroad in Europe were then exposed to the shoe — whether in Norway itself or in London shops that sold that style — and brought it back to the U.S. Fundamental qualities of this style include the lack of laces; the moccasin-like welt across the top; a separate sole with a low heel; and an exposed ankle. Meant to be donned and doffed quickly, it exists somewhere between a more workman-like dress shoe (or even a boot) and a house slipper.
1870s Rogers, Peet & Co. ad - (Image by Ivy Style)
The story continues in Palm Beach, Flordia, then as now a gathering spot of well heeled and well dressed Americans. A staffer at Esquire magazine noticed the shoe in Florida, whence it came to the attention of the publication's founder and editor, Arnold Gingrich. Gingrich saw the Norwegian moccasin’s potential and sought an American manufacturer to produce a locally-made pair. Tapping Rogers Peet, a then-popular but now-defunct American clothier in New York City, to carry the theoretical shoe. Needing a producer, he turned to John R. Bass, proprietor of G.H. Bass and son of its founder.
First Weejuns print ad from 1936 - (Image by Ivy Style)
Bass wasn’t immediately sold on the idea of a leather moccasin — he thought it looked like “a house slipper to be worn outdoors” — but agreed to produce the “Weejun,” supposedly named by some combination of Gingrich and Peet for its Norwegian origins. (They later relinquished the naming rights to Bass.)
After finding an appropriate vendor to produce the soles and uppers and agreeing upon a price point for the shoe, G.H. Bass began production, while Esquire got to work marketing the heck out of it. Touted for its unique combination of durability and comfort, Weejuns were first advertised in print in the May 27, 1936 issue of The New York Herald Tribune. (“First seen at Palm Beach! First at Rogers Peet! First shipment a sell-out!”) The price? $6.50 — not far off, after inflation, to the starting price for a pair in 2025.
It took some years to catch on, but by the 1950s, the Weejun accounted for a significant portion of Bass’s moccasin-style shoe production. Perhaps given its pricing — significantly more affordable than a benchmade dress shoe — or the fact that it could be quickly slipped on or off without fuss, the Weejun quickly caught on with college students. Or, more specifically, with Ivy League types, who paired it with other now-iconic pieces that we were, in the mid-20th century, slowly becoming immortalized in the American sartorial lexicon: Wide-legged khakis and shorts; polo shirts; button-down Oxfords in all manner of pastel shades; tweed; etc.
This was also the era in which the penny loafer took on its famed nickname: A decorative slot atop the leather saddle has just enough space in it for a small coin. Sartorial lore — perhaps apocryphal — states that American college students would stash a penny in this slot for use in a pay phone. However, Bell System pay phones didn’t accept pennies — the smallest accepted denomination was the dime — but perhaps “dime loafer” just didn’t have the same ring to it? Or perhaps the entire story is hogwash, but nevertheless: The name stuck, and whereas the term “Weejun” is bound to elicit a look of confusion from the average millennial or Gen-Zer, “penny loafer” still elicits a knowing nod.
Paul Newman lounging about in a pair of penny loafers - (Image by Old Money Book)
Beyond the Ivy League campus, men who shaped the culture in 1960s America quickly adopted the penny loafer as their own: Ever an adherent to the Ivy League look, Miles Davis wore them on recording sessions, while Elvis slipped them on while relaxing. Actors Cary Grant, Steve McQueen, James Dean, and Paul Newman were all fans, as was John F. Kennedy, perhaps the most “Ivy” of American presidents.
Worn in a relaxed manner, the penny loafer constituted a distinctly American take on footwear. Across the pond, however, powerful men such as the Duke of Windsor chose to wear them with double-breasted suits, turning the casual penny loafer into a more formal accessory. Back in the 1980s in New York City, the penny loafer was adopted by the Wall Street banking class, paired once again to more formal suiting and taking on a distinct yuppie identity.
These days, the penny loafer remains a style staple and a classic choice for semi-formal wear. Inspired by Native American footwear, given a European twist, and brought back to America to great effect, it’s a must-have accessory in any self-respecting sartorialist’s wardrobe. While G.H. Bass — purchased and sold several times since it was established in 1876 in Wilton, Maine — has moved its penny loafer production to El Salvador, it has managed to keep pricing roughly in line with the (inflation-adjusted) MSRP of its 1930s-era shoes. (A boon to college students, to be sure.) Other manufacturers such as Alden still make their shoes in the United States, albeit at higher price points.
Below are some of our favorite penny loafers at different points. Certain manufacturers also make penny loafers in ladies’ and children’s sizes, as well.
G.H. Bass Men’s Larson Weejuns Loafer ($175)
G.H. Bass Men's Larson Weejuns Loafers - CLICK HERE
The O.G. penny loafer. Produced in El Salvador, the unlined Larson — which comes in numerous colorways including two-tone white-and-black and whiskey-and-white — features leather construction; an apron/moccasin toe; and the famous slotted saddle. Affordable and hand-stitched, it’s a classic for a reason.
Allen Edmonds Newman Penny Loafer ($395)
Allen. Edmonds Newman Penny Loafer - CLICK HERE
Another well known American manufacturer, Allen Edmonds was founded in Belgium, Wisconsin in 1922. Though its Newman penny loafer is imported, its wide range of available colors and sizes and excellent construction made it a solid value. (It can be resoled if need be.)
Alden Unlined Leisure Handsewn Moccasin Penny Loafer in Snuff Suede ($710)
Alden Unlined Leisure Handsewn Moccasin Penny Loafers in Snuff Suede - CLICK HERE
Want a made-in-America penny loafer with gorgeous construction and materials? You’ll pay handsomely for it, but this is a “forever” shoe — with its flexible single-leather outsole, van last, and Goodyear welt construction, it’s a true heirloom product.
