It’s official: The penny is on its way out. After 232 years, they’re canceling it, literally. It matters little that they cost three times as much to mint, or that few of us still keep single cents in our wallets—in our heart of hearts, they’ll always belong on the vamp of a great loafer, even after they disappear from circulation.
The penny loafer has been a fixture of American style since the 1930s, when G.H. Bass introduced the “Weejun,” a Scandinavian-inspired slip-on with a tidy little slot just big enough for a coin. Students slipped in pennies for good luck and a cultural icon was born. Penny loafers eventually came to define everything from Ivy League dressing to ’90s minimalism.
Nearly a century later, the shoe’s appeal is broader than ever. The best loafers for women are a true wardrobe workhorse: genderless, ageless, and endlessly adaptable. Fashion insiders wear them with puddled trousers and oversized knits; celebrities sport them year-round with jeans and knits, and preps still swear by a traditional black or oxblood pair that goes with everything.
Part of the loafer’s magic is its range. It can skew crisp and collegiate or subversively cool, polished enough for the office yet relaxed enough for weekend errands. The best penny loafers for women make an excellent anchor for tailoring, dresses, stiff denim, or slouchy layers.
If the demise of the penny has you feeling sentimental, or maybe even a little shortchanged, consider this your excuse to revisit the timeless style it helped make famous. You might need to look elsewhere for a little luck, but as far as penny loafers go, the below are worth every cent.
In for a Penny, in for a Pound
The classic penny loafer, of course, looks great with other staples like a bomber jacket, jeans, and button-ups.
A Pretty Penny
For a cheeky yet mature take on the school-girl skirt and shoes, wear a pleated skirt that hits mid-calf with Miu Miu’s heeled loafers. A suede jacket and a turtleneck take the outfit into fall.
See a Penny, Pick it Up
Timeless with a preppy twist: mix suiting separates with a plaid button-up and black leather penny loafers.
A Penny for Your Thoughts
Rich burgundy loafers pair well with cozy textured clothes, like a knit dress, chunky socks, and a lush camel topper.
When the Penny Drops
Mix a hint of collegiate charm with cool off-duty separates (track pants, hoodie, cap) for a balanced take on high-low dressing.
Shop more penny loafers here and ensure that you keep this timeless style alive even after the penny disappears from circulation.
