Wherever you start on your journey of building a classic menswear wardrobe, you’ll eventually find yourself looking at a page of handsome dress shoes and wondering, “What’s the difference between Oxfords and derbies, anyway?” It’s a good question, and (if you’re serious about footwear) an important one. While one pair of old-school leather lace-ups may look more or less like another to the untrained eye, there’s a world of difference in the details.
The short answer is that Oxfords are more formal than derbies, and the two are primarily differentiated by the way they’re made as well as how they’re laced. And the long answer? Well, let’s get into that.
What is an Oxford?
Much like the vaunted button-down shirts, Oxford shoes are named for Britain’s Oxford University, where these classic kicks first became fashionable in the mid-1800s. As with many great inventions, the Oxford combined two things that were already popular: an ankle boot and a formal dress shoe. Boasting the comfort and versatility of the former and the refinement of the latter, the Oxford’s utility and style proved a winning combination in the 1860s and has retained its appeal ever since.
Oxfords haven’t changed all that much over the last 200 years, and then as now, their key defining feature is a “closed lace” design with the lace holes punched directly into the vamp (the piece of leather covering the top of the shoe). This, along with a typically elongated toe, lends the shoe an altogether sleeker look and makes the Oxford slightly stiffer than its sportier cousin, the derby.
Today, Oxfords remain the standard for business formal dressing—particularly the cap-toe variation, which features a horizontal seam across the toe of the shoe. There’s also the fancier “wholecut” Oxford—crafted entirely from a single, seamless piece of leather—commonly reserved for black-tie occasions.
What is a derby?
Where the Oxford is buttoned-down and formal, the derby by contrast is jaunty and fun. More importantly, especially for those with wider feet, it also tends to be more comfortable. The key difference is that derbies (or DAR-bies if you’re British) are laced via a pair of flaps stitched onto the upper, a distinction that gives them more flexibility.
Like Oxfords, derbies showed up in the mid-1800s and (depending on who you ask) were either named for the 12th Earl of Derby or his grandson, the 14th Earl of Derby. What we know for certain is that, unlike previous designs with closed lacing systems, the derbies’ flaps made them easier to take on and off, and more suited to all-day wear.
The derby was often worn as a more practical countryside shoe, which accounts for the greater variety in styles available—there are sophisticated, slim-soled derbies that would look right at home with a suit, as well as rugged, lug-soled derbies that better paired with jeans and a biker jacket. Perhaps the most iconic modern derby is the Dr. Martens 1461, whose comfy soles and attractive round-toe shape has made it a staple everywhere from the factory floor to the mosh pit.
What about brogues and wingtips?
Rather than entirely different categories, brogues (shoes with those little dots punched in the leather, usually around the toe) and wingtips (brogues with a W-shaped piece of leather stitched across the toe—all wingtips are brogues, but not all brogues are wingtips) are generally subspecies of Oxfords and derbies.
There’s also the saddle shoe, a sporty Oxford variant with a contrast-colored piece of leather over the middle, and the kiltie, a fringed piece of leather over the laces that can appear on either footwear style. All of this variety means that whatever you’re wearing, from corduroys and a chore coat to a black tux, there’s a pair of derbies or Oxfords that’ll work with your look. It also means there’s virtually no limit to how many pairs you can reasonably aspire to own.
