Should You Buy Oxford or Derby Shoes?

If you're new to it, the world of men's dress shoes can be complicated. It can be a bit pretentious with the old-school, rule-follower types who see this guidelines as laws. We're in the middle of that and the new laissez-faire red carpet world. You can and should wear the stuff you like—unless it's black tie, wear black tie—but you should know the rules before you break them. It means you're making choices for yourself, and you're making those choices on purpose.

But because dress shoes do sometimes need to meet an occasion's dress code (weddings and other formal events) it's often better to know and follow the rules. Then, when you want to make an unconventional style choice, you know when and how to do it.

The first step is knowing your shoes. Simple, so long as someone has taught you. Here, we're talking the oxford and the derby. They're the two shoes that are misidentified (or not differentiated) the most often, and that's because they have similar constructions. They're both dress shoes, usually in leather but sometimes in suede, with laces, and probably in black or various shades of brown.

The big difference in the shoe is in the lacing system. The Oxford uses a closed lacing system, and the derby uses an open lacing system. It's just a small detail but it's the detail that matters. Other bits—like a cap toe, a wingtip, or a brogue—can be on both shoe styles.

The Oxford shoe is your fancy shoe, and that comes from a more streamlined silhouette. The "closed" lacing system describes how the leather on the vamp (top of the shoe) is sewn into the quarters (leather around the sides). This is in opposition to the derby's "open" lacing system, which is sewn over the vamp.

If this is confusing, go by our style director's quick tip: "Just look at the top of the shoe, near the eyelets," says Jonathan Evans. "Does it form a "V" instead of a set of parallel lines? You've got an oxford, and that sleek silhouette means you're going to look properly pulled-together for any dressed-up occasion."

The closed lacing system makes the look more sleek because it's sewn right in. That neatness makes them more dressed up. It also makes the vamp a bit more rigid, so you're more likely to need a shoehorn when putting them on, especially for the first few wears. It does not, contrary to what some might say, necessarily make them less comfortable. If you get a last that works for your foot—or on the high end, a last made specifically for your foot—the shoe is going to be plenty comfortable. It's about finding a model that works well with your foot. Besides that, they are your fanciest shoes, and they are fancier the darker and shinier they are.

The derby shoe is slightly more flexible and slightly more casual. That open lacing system (remember, extra fabric that forms parallel lines) means the shoe is more akin to putting on a sneaker. You pull the laces and their flaps apart, loosen up the tongue, and control the tightness a bit more.

Except with a tuxedo, we don't have many rules about when you cannot wear a derby. We like them for this flexibility (in how you can wear it and also the literal flexibility it has while you stuff your feet into it). They are much easier to have fun with because they are just not designed to be as formal as an oxford. You can change them up with suede fabric instead of leather, light colors instead of dark, or go for a chunky construction, like with a pair of Doc Martens derbies.

OK, so remember your difference between an Oxford and derby is in the lacing system—closed and open—and that there are about one-million iterations you can have with either shoe. This, I think, is why people tend to get confused when they hear something like "cap toe" or "brogue" because it feels like the shoe is suddenly a different shape. But it is not. Just remember lacing, lacing, lacing.

A cap toe, wingtip, and brogue are three details you can have on either shoe. A cap toe is just when there's an extra piece of leather around the toe. A wingtip, when that piece of leather looks like wings. Brogue, the punched holes used as decoration around the shoe. You can have a full brogue (perforations all over) with a wingtip, or a half brogue as is. That alone is not enough information to tell us if it's a derby or an Oxford. Although, normally you see more broguing on a derby, which leans into its less-formal look.

In these two shoe types, you can have a ton of styles. If you're thinking formality, remember to go darker, shinier, and more minimalist. A black, leather, whole-cut Oxford will read fancy. A tan, suede, wing-tipped, brogued-out derby will not. Looking for your dress shoes to do the heaviest lifting with the least amount of work? Get a black oxford and a dark brown derby. They will serve you well.