Brooks Brothers (who wants to sell you some) details the (alleged) history of the penny loafer.

The loafer itself was invented in the early 1930s; inspired by an Esquire Magazine photo series featuring Norwegian dairy farmers and their distinctive slip-on shoes. The Spaulding family of New Hampshire, purveyors of leather and lumber, began producing a leather slip-on they called a “loafer”; named after the area on a dairy farm cows “loaf” around in prior to milking.

In 1936 G.H. Bass Shoe Company began producing its famous Weejun, a name meant to give the flavor of the shoe’s NorWEGIAN roots. Mr. Bass’s wife, who sent her husband off each morning with a kiss on the cheek, inspired the distinctive strap detail. Shaped like a pair of lips or the perfect lipstick stain, the new design left just enough room to squeeze in something round and flat.

Two cents won’t get you much these days. There was a time, before the debit card and ATM, when cash payment required the correct dollars and cents. That time is now long gone and the copper penny (now 97.5% zinc), literally, costs more than it’s worth. Back in the 1930s the recently popularized outdoor payphone or “phone booth” cost a paltry two cents. The new loafer design allowed just enough space for a penny in each shoe, equaling the cost of an emergency phone call, thus the penny and the loafer were united, never to be torn asunder.

The penny loafer had its heyday in the late nineteen fifties and early sixties. The shoe became a pervasive trend on Ivy League campuses.

I wonder if the pennies-for-a-phone-call business is true. I’m awfully, horribly old, but I don’t remember pay phones costing less than a dime. My impression was that high school kids put pennies in the slot in the front of the shoe, simply because they would fit there.

We commonly wore penny loafers at Yale in my day, but nobody ever put any pennies in them.

Brooks Brothers is out of luck selling any to me. I still have several pair of so far unused penny loafers purchased from Barrie Ltd. in New Haven, the best purveyor of men’s shoes, now gone, put out of business by the evil Yale Administration in 2003.