How “Weejun” Penny Loafers Got Their Name

If you take a walk around any college campus these days, chances are you’re going to see a lot of Ivy-league inspired styles. Boat shoes, rolled pant legs and Sperry Topsiders are back in a big way. Another popular shoe that never seems to go out of style is the Bass “Weejun” Penny loafer. Here are the story of Bass Weejuns, taken from the book “The Ivy Look,” by J.P. Gaul.

We really can’t say enough about how much we like this book. It is packed with images of vintage advertisements from the height of the Ivy Look era (the late 1950s and early 1960s) and is a celebration of classic men’s fashion. As a bonus, there are a lot of great jazz album covers, too. Who knew jazz and the Ivy look were so interconnected?

Here’s what Gaul has to say about Bass Weejuns…


The original loafer was introduced to America in 1936 by a bootmaker named George Bass, who had made boots for Admiral Byrd’s Antarctic expedition and flying boots that Charles Lindburgh wore on his transatlantic solo flight.

Bass, no novice when it came to footwear, adapted his new shoe from the traditional Norwegian’s fisherman’s slipper, calling it the Weejun in acknowledgement of its Norse origins. Ironically, the Norwegian shoe itself was based on the American Indian moccasin.


The Weejun soon became a symbol of American casual style, worn by men and women alike.

Women slipped pennies into the front and made loafers a fashionable craze. Indeed, Bass Weejuns are known as ‘penny loafers’ to this day.


The Ivy Look

Before the “Preppy Look,” there was the “Ivy Look.” Democratic, stylish, and comfortable, the Ivy Look’s impact and influence can be seen to this day in the clothes of designers such as Ralph Lauren and Giorgio Armani, as well as in the more proletarian offerings of L. L. Bean, J. Crew, Dockers, and Banana Republic. From the button-down hip of Steve McQueen, Paul Newman, and Miles Davis to the enduring style of the cast of Mad Men — they all knew the true cool of the Ivy Look. The Ivy Look digs deep into the vaults to produce the ultimate guide to the genuine article, featuring new, still-life shots of original clothing and accessories plus key examples of the cover art of Blue Note, Stax, Motown, and Atlantic Records. Contemporary magazine advertisements, French New Wave, and key American movie posters and new illustrations bring the Ivy Look into sharp focus.