Let's Look Back: A History Lesson of the Penny Loafer

The first day of fall is nearly here. School is officially in session. Just because. Do you really need a reason to pick up a pair of fit-for-every-man-woman-and-child penny loafers? Because I could go on. But instead, I’ll give you a little history lesson – you know, so you can drop some knowledge when someone (inevitably) admires your new shoes.


Early 1930s
Inspired by slip-ons Norwegian farmers wore in an Esquire spread, the Spauldings, a family of New Hamphire leather and lumber suppliers, invented a leather slip-on of their own and dubbed it the “loafer” – a reference to the area cows “loaf” around in prior to milking.

G.H. Bass & Co. put its own spin on the loafer when it slapped on a distinctive strap. Mrs. Bass sent her husband off with a kiss each morning, thus inspiring a band and the opening, which looks like a pair of lips or a lipstick stain. Coincidentally, the this slot leaves just enough space for a round, flat penny.

At the time, pay phones and phone booths were on the rise. The cost of a call? Just two cents. Two shoes. Two pennies. A pair of penny loafers had just enough space to stash the cash for an emergency phone call. And a duo as significant as peanut butter and jelly was born.

Late 1950s – Early 1960s
Call this era the penny loafer’s heyday. You couldn’t step foot on an Ivy League campus without spotting students decked out in this preppy staple. Whether with socks, no socks, or even white tube socks and shorts (a look to avoid at all costs nowadays), penny loafers were the shoes to wear.

Neon brights. Huge shoulder pads. Spandex. All come to mind when you think of 80s fashion. But preppy styles had a moment, too, and as a bona fide preppy staple, penny loafers flew off the shelves.

Penny loafers are still going strong for every gender and generation. Whether they’re baby’s first dress shoe, a prep-school uniform must, or office-ready accessories, these shoes have taken up a permanent place in fashion. Now go forth and spread the word.

Our Cole Haan Men, Cole Haan Women, and Cole Haan Kids Boutiques open Tuesday, September 10, at 11AM ET.

By Chrissy Makkas, Staff Writer

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