Celebrate Independence Day by paying homage to a timeless American classic: The Penny Loafer.

Penny Loafer History

First introduced in 1930, the loafer has since become an American footwear staple, known for its effortlessly classic style. Leather loafers were first worn by Norwegian dairy farmers. It was not until a family farm in New Hampshire adopted an American version of the leather shoe that the moccasin style became the ‘loafer’ (named after the cows who ‘loafed’ around the farm).  

The signature strap the lays across the toe-box of the shoe contains a slit that was originally purposed to hold pennies in-case the wearer had to make a phone-booth call, thus introducing the ‘penny’ precursor that has stuck with the loafer style.

Classic American Style

The emergence of college prep in the 1950s rocketed the penny loafer to its popularity. Walk on any Ivy League college campus in the from the Kennedy to Regan-era and you’d be sure to come across packs of young gentlemen striding along the brick lined sidewalks wearing sockless penny loafers, denim and blazers.                                                       

James Dean wore his loafers sockless, styled with rolled-up faded jeans, a white v-neck and leather jacket. More often than not Dean finished his kicked back ‘cool kid’ look with slicked back hair and a cigarette hanging from his mouth.


Perhaps the most iconic All-American guy, John F. Kennedy, was known for his classic penny loafer preppy style. President Kennedy paired his penny loafers with suits, strolling across the white house lawn, or with chinos and a sweater on the golf course or boating with his family.

Of course, the Kennedy was not the only president known for his loafers. President Bush and Clinton took to wearing the loafers in a tasseled style.

The laidback heritage style, worn by countless American greats, evokes nostalgia for the American past. Wolf & Shepherd’s Bison Loafers implement updated performance technology within our loafer classic style, better representing the progress of innovation in technology and design that has taken shape since the shoe was first introduced with its wood and nails construction in the ‘30s.