As the weather gets warmer and we inch closer to summer, I most look forward to when I can wear my penny loafers again. I pair them with everything – linen suits, wool trousers and sport coats, chinos and madras shirts, and even the occasional pair of jeans and a button-up. While the style is versatile, however, every pair of pennies may not be. I find that the ones that look best with tailored clothes, for example, don’t go that well with jeans. The difference is all in the detailing.
Every pair of penny loafers has a U-shaped ridge that bounds the top of the toe. On my dark brown calf Edward Greens, this ridge is made with a decorative top stitch that results in a very clean line. On my dark brown suede Rancourts, the uppers and sides are handsewn together to form what’s known as a “moc toe” (moc being short for moccasin). It’s a slightly rougher looking line, and this roughness only becomes more so with time, as moc toes tend to loosen with wear. Finally, my tan-suede Ralph Laurens have the most prominent ridge of all, with the top piece of the leather folded down and stitched to the sides.
Generally speaking, the last two styles are a bit more casual than the first, if only because they’re rougher and more prominent looking. I find that they go better with slim chinos or jeans, but if you have a more casual sensibility with tailored clothing, they could work with those styles as well. Conversely, the decorative skin stitch technique tends to be the dressiest. You can see this a bit more easily when you compare those Rancourts above to these Aldens. Both are very American in style, but the Aldens are just a tad dressier.
Toe Box Shape
All things being equal, the sleeker the toe box, the dressier the shoe. In this regard, my dark brown calf Edward Greens are the dressiest, while the dark brown suede Rancourts are the most casual.
Color and Material
Like with all shoes, black and dark browns tend to look dressier, while lighter colors (and non-traditional colors) will look more casual. Calf also tends to be dressier than shell cordovan or suede. This is especially true over time, as suede “balds” with wear. This is because, while you can hide scuffs on calf with shoe polish, there’s little you can do about scuffs on suede. This isn’t a bad thing, as quality shoes look better well-worn, but it does mean that wear tends to show up more on suede than anything else.
It’s easy, when choosing a penny loafer, to find yourself drawn to whatever looks dressiest and sleekest, but beware. While those styles may suit you, it’s useful to think hard about what you might wear your loafers with. If it’s something like chinos or jeans, you might do better with something made with a moc toe or beefroll (beefrolls refer to the visible stitching on the sides of the penny strap, which resemble a cut of beef tied with cooking string). There’s language in penny loafers that will dictate how you can best wear your shoes. As Charles Eames once said, “The details are not the details. They make the design.”