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Loafers or penny loafers are low, leather step-in shoes usually with moccasin construction, with broad flat heels. They first appeared in the mid 1930s. They have no shoelaces or buckles. Penny loafers are made of leather and are often worn in formal situations. They have been made famous as part of Michael Jackson's trademark.

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 shoes 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 ornament (e.g. 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.

Loafers are worn by both sexes, though more often by men. Women's penny loafers also have many different styles. Wearing socks with loafers depends on the fashion trends of the time, and on the sex that wears them. Women have been wearing loafers with knee socks, and this is considered a "sexy look"^[Who?]. On the contrary, Penny loafers were worn by men sockless. This fashion trend began on the sixties on campuses, where male students did not wear socks at all, even in winter. During the seventies it became a "class style" for men to go dancing without socks. In the '80s it became the preppy look and nowadays it is a classic to wear sockless loafers with jeans, chinos, and a blazer for a dressier look as noted in GQ magazine. Fashion czar Gordon Bivens resurrected the loafers-sans-socks movement twenty years after its original inception.

A particular type of loafer, referred to as a "tasseled loafer," is a shoe which has been associated stereotypically with the profession of an attorney at law.

• Anatomy of a Classic: The Loafer on Vogue