Penny Loafers Are Evolving

As an ex-Catholic school pupil, I have some very particular associations with the penny loafer. I reliably wore a pair of Hushpuppies (in ever escalating sizes, naturally) from kindergarten to sixth grade, paired to Land’s End khakis and green polo shirts. I can even remember the simple joy of wearing them with actual pennies inserted into their penny keeper slots, whose infinitesimal monetary value was dwarfed by their shiny copper glow.

But the penny loafers, along with the husky-sized non-iron khakis, were kicked to the curb upon graduation. It’s not that I didn’t need a non-sneaker shoe in rotation—I kept it Catholic until 10th grade and finished at a dismal prep school—but the penny loafer suddenly felt childish, nerdy, or plain uncool.

I’m not sure where these feelings stemmed from. Certainly, an adult-sized Hushuppy would have been preferable to the squared-toe slip-ons I relied on until the blissful release of graduation. But recalling my innocent, grade school-era era enthusiasm for showing them off with actual U.S. currency, there seemed to be something pure and earnest about the penny loafer. And naturally, there’s nothing less cool to jaded teenagers than being earnest. 

I suspect that’s why many of us drift into sneakerdom in early adulthood. Unlike leather-soled shoes that suggest you may be on your way to church (with a nicely creased pair of khakis and a fresh polo shirt, naturally), scuffed sneakers signal that no one—not parents, teachers, or even a girlfriend—is dictating where you’re going and how you will dress for it.

Before we continue, I confess that I never was much of a sneaker guy myself. I relied on Adidas Sambas through college but came back to the penny loafer after discovering Ivy style post-graduation. In particular, I’m a fan of Rancourt’s beefroll penny loafers, which are made in Maine and have every Take Ivy detail imaginable including moccasin stitching and the eponymous “beefrolls” that frame the penny keeper. If you’re anything of a traditionalist, these are the way to go (and if you can afford it, Alden’s Leisure Hand Sewn is an icon for a reason). 

But it does seem like the high tide of sneaker culture—and broadly, streetwear—has passed, and that enthusiasm for both is waning. However, guys who were obsessing over Yeezy 350s yesterday aren’t going to be slipping into Edward Green oxfords tomorrow. There needs to be a middle ground for getting back into leather footwear, and that medium is the penny loafer.

However, it needn’t be like the Ivy classics outlined above, or the sleeker pennies produced by the likes of Sid Mashburn or Tod’s.  Instead, this new class is made of penny loafers that feel like they may have been sneakers in a past life. Perhaps the best example comes from Brooklyn’s Blackstock & Weber, whose Ellis penny stands tall with a chunky Vibram outsole and is available in everything from a conservative chocolate pebbled leather to daring two-tones and even leopard print. 

See Also

The History of Ivy Boy

Across the pond, Drake’s has introduced an Italian-made Canal penny loafer named in honor of their latest New York store. It take’s the label’s “relaxed elegance” motto to heart, with a rounded last, soft suede upper, crepe sole, and an elliptically shaped keeper that won’t be holding pennies anytime soon. 

Another relevant example comes from L.A.’s Fear of God, which interrupted their minimalist programming to deliver a moccasin-stitched penny with a sleek strap and a rectangular keeper that makes me think of the coin slot on a piggy bank. 

What all these disparate pennies have in common is that they’ve moved the dial a little further from tradition, and in the process achieved what we all aspire towards today: being a bit less expected, and a lot more interesting. Here’s to hoping that they’re merely the vanguard of a coming penny loafer renaissance.