The Penny Loafer

Get yourself a pair now, but consider saving the penny for the wishing well.

Illustration: Jameson SimpsonAh, the penny loafer—icon of preppy style and stalwart of the U.S. footwear scene for 75 years. How fitting that such a quintessentially American shoe should hail from… Norway?

The shoe that so immediately calls to mind a deluge of homegrown imagery actually got its start on the feet of Scandinavian cattle farmers, whose flat, moccasin-style kicks were reinterpreted for the U.S. market in 1933 by the Spaulding Leather Company. In 1936, G.H. Bass got in on the act with their Weejuns (short for Norwegians).

Looking to distinguish their shoes from the competition, Bass added a leather band across the vamp, complete with a small cutout meant to look like a pair of lips. The style took off, and it didn’t take long for people to realize that the cutout was the perfect place to stash a coin—to cover emergency phone calls at first, and purely for style reasons once “dropping a dime” evolved into “dropping a quarter.” The shoes became known as penny loafers, and over the next few decades, they ran rampant throughout college campuses, earning serious cred on the feet of gents like JFK and James Dean before returning to punctuate the uniform of Alex P. Keaton wannabes in the ’80s.

Now penny loafers have made their way to the forefront of style once more. You can, of course, wear them with chinos and a blazer, but you’re also free to rough ‘em up a bit. Try pairing them with cuffed denim and a western shirt, or with shorts and a chambray button-down when summer’s really blazing. Socks—and penny—are strictly optional.

Shop loafers on Gilt MAN >

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