Long before sneakers dominated the casual footwear space, humble black derby shoes reigned supreme. Back then, the derby’s open-lace look made it a staple of off-duty style, the hard-bottom you turned to when pulling on a pair of wingtips felt a little too corporate takeover-y. (We’d say it was prized for its “relaxed vibes”, but that’s an anachronism so extreme it kind of strains the limits of credulity.) But you’d have to be a peculiar type of menswear enthusiast to consider the derby casual today…right? Well, not quite.
Over the last couple of years, the derby made a concentrated effort to reclaim its rightful place in the hearts—and closets—of stylish dudes across the planet. And the PR push paid off. The numbers might not exactly show it, but in the popular menswear psyche the sneaker’s supremacy is in flux, and along with loafers, derbies stand to gain the most from its fall. Because a lot of things have changed since the derby first rose to prominence, but one thing hasn’t: the silhouette is still one of the most versatile on the planet, especially in black.
Don’t believe us? Try one of the very best black derby shoes out for size and then circle back. From exquisitely-made designer riffs to cushy, dependable classics that cost less than a boozy night out, there’s an option here for you. Somewhere on the shoe rack in your hallway, your sneakers are quaking.
The Everyday Pick
Dr. Martens’ 1461 shoe is the rare derby that looks just as good with jeans as it does with a suit. Mostly, though, that’s because the 1461 looks good with everything: baggy denim, slouchy trousers, crisp work pants. (Its endless versatility comes down to the brand’s tough-as-hell leather make and signature rubber soles.) And when the time comes to suit up and you can’t resist reaching for your Docs, give in to the temptation—just print out this picture of Frank Ocean and go on your merry way.
The Suit-Ready Pick
If you chucked your last pair of dress shoes sometime around March 2020, a no-frills pair of derbies is an easy way to ease your feet back into their leather clutches without giving them a nasty shock. Plenty of the options on this list are made for casual wear, but Allen Edmonds takes the opposite track. The pared-down design and modest shape makes them ideal for every formal-ish wedding on your suddenly-packed social calendar, but they’ll look swell anchoring your trusty navy suit when you knock the cobwebs off that guy, too.
The Très Chic Pick
Plenty of derbies aspire to the polish of their dress shoe counterparts, but few attempt to approximate the heft of your favorite retro sneakers. Paraboot’s been making some version of the Michael since the ‘40s, and by now the cult-loved French brand has the equation down pat. Sturdy-as-hell leather uppers + waterproof Norwegian welt + chunky rubber sole = wholly unique silhouette that’s as versatile as a pair of New Balances. You could wear them with a giant pair of chinos and a hardy chore coat, but if you’re eager to break in your pair before the leaves change color, make like Tyler, the Creator (Paraboot appreciator par excellence) and go with a sweater vest, silk neckerchief, pleated shorts, and scrunched camp socks.
The Designer Pick
What makes a plain black derby worth well over a grand? Depends who you ask. Pose the question to a Prada Guy, and he’ll tell you, in no uncertain terms, that’s the brand’s pedigree is enough to justify the price. But press him on the point, and he’ll start waxing eloquent on the mind-meld between Raf Simons and Muiccia Prada, and the way they subtly thumb their noses at the conventions of anodyne office attire, breathing fresh life into sharp tailoring, pointdexter-y knits, and—yes—sturdy black hard-bottoms. And, he might say (getting a little agitated now), much like the brand’s slick nylon sportswear, Prada’s derbies are practical but deceptively thoughtful, cut from supple leather plopped on top of stacked rubber soles. If, at this juncture in the conversation, the manic look in his eyes is starting to make you feel a little on edge, now’s the time to bail. But if everything he’s saying is making a whole lot of sense, well, we probably should’ve warned you about the one side effect of engaging a Prada Guy in serious conversation about derbies: you’re apt to become a Prada Guy, too—and cop the same pair as him.
The Comfort-First Pick
When Nathan Clark introduced his crepe-soled desert boot in the ‘50s, he couldn’t have anticipated how popular his signature shoe would become. (So popular, in fact, that we’ve sung its praises at length, many, many times before.) So when we say its low-top counterpart might be even better than the OG, you know we’re serious. The Desert Khan is a new-ish riff on the silhouette built on top of the same cushy rubber soles that made its older brother a smash. Looking for a derby that doesn’t feel remotely like a derby—at least any version you’ve laced up before? Look no further.