Short Introduction to Penny Loafers


The History

Loafers—which include our classic penny variety—are based on traditional moccasin styles that were worn by Native Americans. While many say that loafers became popular in the 1930s, slippers worn by early settlers in America were worn since the time of the early settlers and are based on the traditional moccasin shape, too.

Loafers were worn by Europeans, and Norwegian farmers brought the loafer shape to the U.S. in the ’30s. These shoes worn by workers fit below the ankles with no buttons or tie closures. They had a low heel, and were surprising similar to the loafers we wear today.

All loafers, including penny styles and the tasseled variety, are constructed from a thick, heavy leather in either brown or black. Wears yours in mahogany brown leather if you plan on keeping them casual.


Penny loafers have ruled the scene for so long that now they’re a classic staple. They can be worn as a casual shoe and should be paired with clothes that represent that. Wear khakis and casual pants with your penny loafers, as well as dressy shorts. You can also wear casual suits in a relaxed suiting and sport jackets.

You can also wear your loafers with a casual suit. While these suits aren’t as popular as they once were, bring back some old style and take your penny loafers along for the ride, too. Linen and seersucker suits fit the bill nicely, as do any casual suits you would wear to a daytime family event or dressy casual party.

In the ’90s, wearing socks with loafers was the norm. With retro trends back, penny loafers have been primarily worn without socks. Prevent nasty blisters and chafing by sprinkling powder inside the shoes and applying a film of Vaseline on the backs of your heels.

If you want to wear loafers for a dressier effect, try glossy loafers in another version besides penny, such as the tassel variety.