Penny for Your Thoughts: A Guide to the Penny Loafer

While the Crosby is our vision of the perfect year-round shoe, for summer, only a loafer will suffice.

Pairing equally with denim as with cotton and linen tailoring, to opt for a loafer is to embrace the season. 

Characteristically, the loafer is a lace-less, low-worn shoe, similar to the moccasin but for a separate sole and heel. Worn casually, the original intention being a “house-shoe” of sorts one could easily slip on and off.

First seen in the form of the 1926 royally-commissioned Wildsmith loafer made for King George VI (to wear indoors with his shooting hose), and the “Aurland Moccasin”, first debuted in 1930 by Norwegian shoemaker Nils Gregoriusson Tveranger (influenced by the footwear of the Iroquois peoples of North America) and named for his hometown. This latter model was adopted by the Spaulding Leather Co. to considerable success.

A cobbler applies moccasin stitching to a pair of loafers. Aurland, 1960s

The term “loafer” originates from the “loafing area” on a farm where cows are taken for milking, it was here that Norwegian farmers would require a flat, slip-on shoe that could be worn outdoors and avoid dragging mud through the home. The first occurrence of the term in it’s modern use is from an article in Esquire magazine dated 1932.

It was in 1936 that the throat line was lowered and a distinctive strap was added to the top of the vamp. The strap had a diamond slit sized just right to hold a penny, ergo the moniker. Later models also sported “beef rolls” on the sides of the strap to provide added structural support.

It was writers such as F. Scott Fitzgerald whom were first seen wearing such styles on their return to America from their travels overseas. The look was soon adopted by the Ivy League college students and became known as the quintessential “collegiate shoe” - along with white bucks and saddle shoes, the penny loafer had become de rigueur on campus. 

Drake's Brown Suede Canal Penny Loafer with Crepe Sole

Legend has it that in the late 30’s, Ivy League students would slip two dimes into the slits on their loafers, this emergency money would provide the means to make that all important phone call when “school funds” needed replenishing. This soon changed to the shinier penny, as necessity gave way to style. Today, a loafer with a penny inserted provides a coded nod to those in the know.

Like so many items of Ivy League apparel, the penny loafer found itself in Britain through the modernist scene of the late 1950s, and it’s penchant for all things American. The penny loafer has since transcended from mid-century student attire into a modern staple alongside the Shetland jumper, chino trousers, and Oxford shirt.

The penny loafer has seen itself modelled on countless sartorial influencers, President John F. Kennedy, James Dean, Gene Kelly, and the Duke of Windsor who, amongst countless other things, first popularised the wearing of the Penny loafer with suits in the 1930’s.

Gene Kelly in Les Girls, 1957

Whilst once worn only as part of casual attire, nowadays the Loafer can be teamed with a suit and still retain a sense of formality. This is due in no small part also to the increase in airport and building security in the 1980s, when time is money, Wall St. stockbrokers could not afford to be held up tying their laces.

Amongst Ivy-style purists there is a long-held tradition of subjecting one’s loafers to an endurance contest of sorts, letting them become as worn as possible, often taking to the application of Duct tape to literally hold them together - not a problem with our handmade loafers, look after them, and they’ll look after you.

Drake's Black Leather Charles Goodyear Welted Penny Loafer

As part of our range of in-house footwear, we developed two iterations of the penny loafer, the crepe-soled Canal, named for our Open Studio in Manhattan, and the Charles, a Goodyear welted, distinctively sleek version best paired with our casual tailoring but an apt companion to denim, linens, tweeds and chinos alike.

SHOP LOAFERS