Style Defined: Penny Loafers

A short primer on the history of the penny loafer

If there was ever a piece to encapsulate that iconic ‘prep’ style, it may be the penny loafer. Appropriately, it’s a shoe with a quirky and interesting background as well.

Perhaps the best way to approach the history of the penny loafer is to dissect the name of the gold standard – the Bass Weejun Penny Loafer. So let’s take it one word at a time.

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First, let’s take a look at the ‘loafer’ part, which is pretty simple. Penny loafers are, well, loafers, which is to say that they are a slip-on shoe, rather than a laced shoe such as a brogue or an Oxford. This kind of shoe has been around for ages, whether you’re looking at the moccasins of native americans or the slip-on dress shoes of European aristocracy.

‘Weejun’ is actually short for Norwegian

Moving on, let’s hit ‘Weejun’ next. Surprisingly enough, ‘weejun’ is actually short for ‘Norwegian,’ and is actually the first tie-in for the shoe with the academic, ‘Ivy’ crowd.

Word has it is that students traveling to Scandinavia in the early 1900s spotted Norwegian fishermen wearing a simple, comfortable style of loafer constructed like a moccasin – almost the penny loafer. They brought the style back to North America, where it gained a cult following.

G.H. Bass and the Bass Weejun Penny Loafer

Bass is next. G.H. Bass founded his namesake company in 1876, but it wasn’t until 1936 that they really made their imprint on men’s style as they became the first company to mass market the ‘Weejun’ loafer style (trademarking the name as they went).

Rather than introduce just a simple loafer, they decided to add a decorative, fashion-oriented touch by including a strap running horizontally across the vamp of the loafer.

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Which brings us to the final element, the penny! This above named strap happened to be cut in what can only be described as a ‘lip-like’ shape, with a small opening at the center that happened to be the perfect size and shape for a small, round object like a penny.

Serendipitously, this was also back when a phone call cost just that – a penny. This was perfect for students who were drawn to the look as the subtly flashy – that’s a thing, right? – embellishment carried a handy, practical application for that just-in-case emergency call home.

Penny loafer then and now

The shoe has come a long way from its fisherman roots. As mentioned, it was eagerly adopted by Ivy Leaguers and became firmly ensconced in the canon ‘preppy’ men’s style but it traveled even farther than that. These days, the style has been covered by every high fashion designer out there, and has been paired with suits, shorts, jeans, trousers, you name it.

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What’s the best way to wear penny loafers?

For the everyman trying to work it into their wardrobe? The safe move is to keep it a casual style. Penny loafers work pretty well with jeans, definitely work great with chinos, and can really only be pulled off with a suit in the perfect conditions.

If you want to pay homage to those preppy roots, rock a pair with kahkis, a navy blazer, an OCBD and a knit tie and be as preppy as preppy can be. Or follow James Dean’s lead and go mid-century rebel with dark denim and white t-shirt. The options are copious.

In all reality, your biggest decision is probably – socks, or not? The answer is a bit contested, but I say let those ankles breathe. And if you’re nervous about foot sweat and stink, try some no-show loafer socks.

Thanks for reading,

Stylishly Yours,

Adam Lehman
He Spoke Style

Chime In

  • eli G.

    Great article! I love how you tied in those stories. I’m looking to buy my first pair of penny loafers and I’m looking in the direction of Cole Haan