Penny loafers are low, leather step-in shoes whose tops resemble a moccasin, but have broad flat heels. They first appeared in the mid 1930's. They have no shoelaces or buckles. Penny loafers are made of leather and are often worn in formal situations.

The men's fashion and lifestyle magazine Esquire photographed dairy farmers in Norway wearing slip-on shoes around the cattle loafing area (where dairy cows gather to await milking). American lumber and leather interests owned by the Spaulding family in New Hampshire started making loafers based on these photographs in about 1932 or 1933 - naming them loafers. They were also called ponies by some - often women would slip a foot out of one shoe and rest their toes on the counter (back) thus appeared to be standing as a pony often will with one leg resting on the very tip of its hoof. In 1934 John R. Bass (a bootmaker in Wilton, Maine) started making loafers and called them Weejuns (meant to sound like Norwegian). These had a strap across the upper part of the vamp that was shaped like a pair of lips (said to be John's wife, Alice Bass, kissing each shoe on its way out the door). The mouth opening soon was used to hold an ornamentation - perhaps a penny and thus penny loafers became a style. Penny loafers often held a dime instead of a penny. If a girl's date got out of line she could call home on a pay phone--which accepted dimes during most of the fifties and sixties.

Penny loafers are worn by both sexes, though more often by men. Women's penny loafers also have many different styles.