19 Best Black Derby Shoes 2023: Crucial Kicks From Prada, Dr. Martens & Paraboot


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.

The Best Black Derby Shoes Shopping Guide

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 derby shoes

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

Allen Edmonds Leeds plain toe derby

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 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 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, 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

Camper “Walden” plain toe derby

Before sneakers were sneakers, crepe-soled shoes were the kings of comfort. And while there are plenty of derby-sneaker hybrids on the market right now, they tend to feel more like chimeras than pegasuses. Camper’s, though, is the rare hybrid style you can dress up for a black-tie event and still manage to give your tired dogs some well-deserved respite.

The Senior-Approved Pick

Remember those mysterious, unbranded hard candies—you know, the ones that you’d only ever see in your grandparent’s foyer but never at an actual store? Paraboot was kind of like that for a long time. They were one of those shoes that seemingly every swaggy septagenerian knew about but were hard to track down IRL. (Did you have to be an AARP member or something?) Paraboot’s charming old man-esque shoes are easier than ever to acquire these days, and once you do, you’ll never want to take them off. They’re made with tough, top-notch leather and built with a super-durable Norwegian welt construction to last you until you’re actually old enough to stockpile your own mysterious candies.

The Value Pick

Solovair 3 Eye Gibson shoe

Solovair’s shoes are made in the UK in a generations-old factory, and represent some the best bang for your buck on the planet. They’re built with a Goodyear-welt construction, which means they can easily be resoled by a cobbler several times over before you have to put them out to pasture (you’re looking at a decade or more of wear, FYI). The break-in period is something you’ll have to be mentally prepared for, but the bouncy soles and synthetic footbed make the process bearable. And, unlike most leather sole derbies, these are made to be beaten, not babied—they were originally made for the British army, after all.

Plus 13 More Black Derbies We Love

Morjas plain toe blucher

Morjas is a relative newcomer, but it’s already made waves thanks to its beautiful designs and heritage-level quality. These pebble-grained bluchers sand down the edges of most plain-toe options, but look just as handsome with a suit as they do with vintage jeans.

J.Crew Ludlow derbys

Pssst—J.Crew’s in-house shoes are also made with Goodyear welted construction, and you can find them on sale pretty often. But you didn’t hear that from us.

Tricker’s Bourton leather wingtip brogues

Tricker’s made its name on shoes built for trudging through the wet English countryside. We may not think of a pair of wingtip brogues as knockabout kicks anymore, but the brand’s quality and style remains as covetable as ever.

Kleman Padror shoes

Crafted in France, the Kleman Padror is a traditional Tyrolean walking shoe that you’re likely to see on the feet of the local dripped-out granddads. Pair ‘em with some baggy chinos and a cardigan and you’re ready to hit the farmer’s market in style.

Raf Simons glossed-leather derby shoes

Like a glossy block of onyx, these Raf Simons derbies are a sartorial sculpture that’ll pump up every outfit.

Alden Cordovan plain toe blucher

Shell cordovan leather is coveted for its sheen, texture, durability and rarity—and out of the myriad options that use it, Alden’s classic plain toe blucher is the aspirational grail for every menswear guy’s closet.

Thom Browne classic longwing brogue

Thom Browne’s iconic wingtip brogues haven’t missed a red carpet appearance probably, uh, ever. They’ve got a classic design with a signature TB flair that’s enough to sweep any black tie event with panache without wandering into gaudy territory.

Velasca Cumenda blucher

Slick and shiny enough to pass as a glossy patent leather pump, Velasca’s Cumenda bluchers would turn heads at a black tie event and get you some big ups at the office.

Lemaire square derbys

Square up!

Guidi 79082V derbys

Guidi’s artisanal approach to footwear has earned it a dedicated following of fashion nerds who extol natural dyes, antique techniques, and avant-garde designs.

Beckett Simonon “Anders” split toe derbies

Splitting hairs over how much to spend on a new pair of go-to stompers? Fork over a measly $200 for these split-toe beauts and never look back—unless it’s to check your reflection in the mirror.

Maison Margiela Tabi lace-up derbys

If there’s one shoe that can instantly virtue signal your taste for capital-F Fashion it’s Margiela tabis, with their head-turning, hoof-adjacent split toes.

John Lobb “Arron” full-grain leather derby shoes

John Lobb is a god among cobbler, and it’s hard to choose just one pair from their selection. But these grain-y split-toe babies balance a chic dressy-ness with a casual country ruggedness—and they’re just plain ol’ gorgeous, to boot. 

Fashion Desk

Fashion Desk is the official writing team behind the renowned Fashion Daily Magazine, a leading authority in the world of fashion. Composed of a collective of passionate fashion journalists, trend analysts, and style editors, Fashion Desk provides insightful, up-to-the-minute coverage of the latest trends, fashion news, designer showcases, and style inspirations.

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