A Pretty Penny

The loafer is the shoe you want to wear right now. Here’s how to do it right.

A Pretty Penny - YAM Magazine Mar/Apr 2024
The Liv Loafer from Free People incorporates a “coin” right into the design.

By Liam Razzell

As people, places and things age, the murkier their origin stories get. And that’s true for penny loafers — a century-old shoe that’s both a classic and the trendy footwear of the moment. But where, and with whom, did they originate?

Some argue the shoes date back to rural Norway. In the 1800s, British travellers visited small Norwegian towns to fish for salmon. There they were exposed to leather slip-ons called “tesers” worn by the locals. Some of these anglers took the shoes back home, and therefore spread the style internationally.

Others say that moccasins — leather slip-ons worn by Indigenous people in Canada and the United States — inspired the first penny-loafer designs. Traditionally made from animal skin, the low-top versions of these shoes look similar to penny loafers, though they don’t have a heel or an instep strap.

Then there are those who claim London shoemaker Raymond Lewis Wildsmith made a slip-on shoe similar to penny loafers for King George IV, Britain’s monarch from 1820 until his death in 1830.

There are also examples of leather slip-ons from around the world that existed long before penny loafers did.

Whatever its origin, shoemaker Nils Gregoriusson Tveranger is cited as the father of the modern-day penny loafer. Born in Norway in 1874, Tveranger studied shoemaking in the U.S. until he returned to Norway, where he patented a shoe he’d been working on called the Aurland moccasin. Inspired by Indigenous moccasins and Norwegian tesers, these shoes were soon available for purchase across Europe.

Enter Esquire. In the 1930s, the men’s magazine partnered with retailer Rogers, Pete & Co. and Maine-based manufacturer G.H. Bass to produce their take on the Aurland moccasin. These shoes, called Weejuns (short for “Norwegians”)  introduced Americans to the style, which soon became popular with young trendsetters — many of whom wore loafers casually — and others looking for fresh, versatile dress shoes.

But why “penny” loafers? Some say it’s because people used to keep a penny in each shoe’s instep strap to make pay-phone calls, but it’s unclear whether that’s true or how the trend started — it may have just begun as a simple way to accessorize the shoes.

A Timeless Outfit

Penny loafers have only grown in popularity since their rise in the 1930s. Today, they come in a variety of materials, designs and styles, and are worn around the world by men and women alike. (Three super-popular loafers right now are the Dr. Martens Penton, Solovair Hi Shine and G.H. Bass Logan Flat Strap Weejuns.) 

A Pretty Penny - YAM Magazine Mar/Apr 2024
G.H. Bass Weejuns.
A Pretty Penny - YAM Magazine Mar/Apr 2024
Solovair Hi Shine Tassel Loafer.
A Pretty Penny - YAM Magazine Mar/Apr 2024
MR P. Scott Low-Cut Leather Loafers.

As Janine Metcalfe, YAM’s fashion editor, says, “Fashion is cyclical, but loafers never really go out of style.” 

For a timeless outfit, pair the shoes with nice socks, a belt, a T-shirt and jeans in black, dark blue or light wash. Perfect for a night at the bar, casual work functions and running errands, for both men and women. This is the easiest, least expensive way to style penny loafers. Because the combination is so simple, it’s great for incorporating accessories and layers — overshirts, sweaters, jackets, scarves, tuques — in winter months. 

But there are a few things to keep in mind.

Socks matter. Contrary to the views of suiting aficionados, white socks pair with penny loafers. White sports socks will do in a pinch, but only if the grey soles that many have don’t show. Solid-colour dress socks will catch the eye, make loafers and jeans pop and add a sense of fun to the outfit. Or go sock-free — ideal for casual looks and hot summer days. When wearing dresses and skirts with loafers, women can sport thicker, textural socks. 

A Pretty Penny - YAM Magazine Mar/Apr 2024
Hand-painted Wilde Orange penny loafer from Duke + Dexter.
A Pretty Penny - YAM Magazine Mar/Apr 2024
Dr. Martens Penton Floral Jacquard Loafer.

Jeans are important, too. Dark jeans help create a streamlined look, especially when paired with a similar-coloured T-shirt. Patched, stained, paint-splotched and fraying vintage jeans nicely contrast the loafer’s sleek, polished look. 

Also, wide-legged pants look better with chunkier loafers, and vice versa. For example, a pair of bulky, platform penny loafers with uber-slim jeans can make feet look clown-ish, but sleek, traditional ones with baggy, wide-legged jeans can make feet look small. Where pants fall is also important. Long, baggy jeans look great with lug-sole loafers, but to make the shoes the outfit’s centrepiece, show them off by cuffing jeans or wearing a cropped or ankle-length pair.

When wearing accessories, think about how they’ll complement loafers. “If your loafers have a bold pattern or are heavily embellished, avoid wearing too many attention-grabbing accessories,” writes Sarah D’Arcey, a Vancouver-based stylist who has dressed actors for Netflix and Warner Bros., in an email. “I recommend creating a harmonious look, not a competing one.”

That advice applies to T-shirts, too. Big graphics compete with flashy loafers. As a rule of thumb, plain T-shirts are best. And when tucking a T-shirt into jeans, complement loafers with a matching belt — black loafers, black belt; textured loafers, textured belt — to add continuity.

Step Up Your Loafer Style

Jeans + T-shirt + loafers (with or without socks) is a classic combination, but it’s not the only way to style this classic footwear. Here are six other outfits to pair with standard black penny loafers:

Illustrations By: Janice Hildybrant

A Pretty Penny - YAM Magazine Mar/Apr 2024

Skirt or colourful, flowy dress; chunky white socks.

Oxford-cloth button down; shorts; no socks.

A Pretty Penny - YAM Magazine Mar/Apr 2024

White T-shirt; black V-neck sweater or sweater vest; black pleated trousers; white socks.

Chunky sweater; high-waisted, wide-legged, pleated chinos; socks optional.

A Pretty Penny - YAM Magazine Mar/Apr 2024
A Pretty Penny - YAM Magazine Mar/Apr 2024

Monochrome suit or skirt suit; colourful socks.