23 Best Chelsea Boots for Men in 2023: Slick, Streamlined Shoes to Wear With Everything

23 Best Chelsea Boots for Men in 2023: Slick, Streamlined Shoes to Wear With Everything

It might be a while since you last seriously considered the best Chelsea boots for men. We’re a few years out from the style’s heyday, and much has changed in the wild world of men’s fashion. But the Chelsea boot is still here, its spirit wholly undeterred by the shifting preferences of fickle footwear connoisseurs around the world. Trends? Ha! The Chelsea boot scoffs at trends. Ever since its midcentury rise on the streets of Swinging London, it’s seen more of them come and go than it cares to remember. It earned its coveted “essential” status the hard way: by actually living up to the honorific. So bring on the funky, fur-covered mules and the trail-ready sneaker hybrids. (No, really. Bring ’em on. It’s been a minute since the Chelsea boot had a nice laugh.) 

The Best Chelsea Boots Shopping Guide

At their core, the best Chelsea boots for men are defined by two important details: an ankle-hitting height and an upper constructed from two pieces of sewn-together leather. (The most common silhouette also features a panel of elastic that unites the two parts on either side.) But the key element to any Chelsea boot that aspires to Keith Richards–during-tax-exile greatness is the shape of the toe. The rule of thumb used to be that the more tapered the toe, the dressier the shoe. That meant you wanted something that’s neither severely pointy nor clown-shoe huge– the shape would look sort of like the top of an egg: round but not too round. (And if you’re looking to get a little freaky, maybe even a little bit squared.) 

Sure, the Chelsea boot’s limelight may have dimmed ever so slightly over the last few years, but if 2022 turns out to be the decadent return to form it’s shaping up to be, we wouldn’t count the shoe out yet. A thanks to the sheer popularity of the silhouette, chances are there’s a great pair out there for you at this very moment. Whether you’ve got $100 or $1,000 to blow, these are the best wear-with-everything Chelsea boots to buy right now. 

The Chelsea Boot

Saint Laurent “Wyatt” Chelsea boots

It was over a decade ago that Yves Saint Laurent’s ready-to-wear collections were rebranded Saint Laurent and the house’s aesthetic was overhauled from all things French and luxe and proper to only things bohemian, punk, and badass. And the anchor to every look then—and even now, post–Hedi Slimane, under the creative direction of Anthony Vaccarello—was a pair of sleek Chelsea boots. These boots, actually. The Wyatt is an archetypal black Chelsea boot, crafted in Italy out of calfskin leather that’s durable but still pliable (crucial for a shoe like this, which you want to look great but also to actually walk in—a lot). These are the standard-bearers because of all the tiny details they just absolutely crush: the ankle-hugging elastic, the almond-toe silhouette, and a smartly designed pull tab hidden inside the back that makes getting these on and off a breeze. Sure, they’re not cheap. But if you want the Rolex of Chelsea boots, then you want these boots.

The All-Purpose Chelsea Boot

R.M. Williams “Gardener” whole-cut leather Chelsea boots

R.M. Williams’ Gardener boots bridge the gap between dressy and casual better than any other on this list. They’re well-suited for pairing with a, uh, suit when you mean business, or with tried-and-true blue jeans when you want to hit the great outdoors (and by “hit the great outdoors”, we mean anything from attending a barn wedding to navigating the checkout line at Trader Joe’s). The toes on these are scalpel sharp—trim and beveled, rather than round and bulbous—which means they’ll look awfully good with anything slim and tailored, but don’t be afraid to wear ’em with wide-leg cords (or, hell, some cuffed work pants), either. 

The No-Frills Chelsea Boot

New Republic “Sonoma” suede Chelsea boot

The magic of Chelsea boots? If you grab the right pair, they can totally change your point of view. Conveniently, this is exactly what happened to GQ contributor Clay Skipper. “Clothes have never really been my thing,” he writes. And yet, after he picked up a pair of New Republic boots—sandy suede, cushy crepe sole, happy-making $128 price tag—the whole world shifted on its axis. “Walking to dinner one night, I felt like I’d finally slid into the slipstream, one more figure in the nightly parade of fashionable New Yorkers,” he says. “Even at dinner, my boots hidden under the table, I got an added dose of confidence just from knowing they were there. Also: The insoles feel like walking on memory-foam pillows.” Confidence-boosting, fashionable-making, pillow-walking boots at this price tag? Hard to turn down.

The Slightly-More-Frills Chelsea Boot

Common Projects suede Chelsea boots

If this isn’t your first Chelsea boot rodeo, consider Common Projects. CP, of course, is the Italian label that turned super-minimal white sneakers into office- and wedding-grade attire. So when those footwear wizards turned their attention to the Chelsea boot, magic was bound to happen. Lo and behold, it did—which is roughly how you explain every fashionable dude you know getting into multiple pairs. These come in suede, and add the high-cushion crepe outsole—and you get the brand’s signature heel-stamped gold lettering tossed in, too. Like everything else Common Projects makes, these boots find the happy medium between edgy continent-hopping DJ and elegant suited man, which means you can easily sport them at the office and on your next bar crawl (just try not to spill all your beer on them).

The Crappy Weather Chelsea Boot

Bludstone 500 chelsea boots

Some Chelsea boots lean heavily into their rockstar appeal, while others skew utilitarian, expressly designed to protect you from the elements. Then there are the rare pairs that gracefully straddle the line between, like this all-weather riff from the Australian footwear maestros at Blundstone. Those tough leather uppers might not be monsoon-ready, but on days when you just need to jump a few puddles en route to work, the whole package is the slickest way to ensure your socks stay dry without compromising your fit.

The Chelsea (by Way of Texas by Way of Paris) Boot

Celine cruiser Chelsea boots

Celine frontman Hedi Slimane made his name cranking up the volume on classic rock ’n’ roll styles, imbuing the staples of the genre—hip-hugging flared jeans, bedazzled leather jackets, shrunken tuxedo blazers—with a jolt of Parisian cool. So it doesn’t come as much of a surprise that a shoe popularized by a little group called The Beatles is prime fodder for his latest hit design. What is surprising, though, is the far-reaching source material Slimane pulls from here. Forget stage-ready: Celine’s Chelsea boots look downright rodeo-ready, a closer relative to cowboy boots (see: the contrast stitching, the pointed toes, the stacked heels) than anything your newly-interested-in-menswear pal already owns. If sleek black Chelsea boots—the kind John, Paul, Ringo, and George wore regularly—represented the rock god epitome of the style for the last decade or so, these guys make a strong case for expanding your horizons the next time you need a pair—and maybe booking a ticket to Austin while you’re at it.

Plus 17 More Chelsea Boots We Love

Saint Crispin’s plain boot

It might not boast the centuries of history that some of its French and British counterparts do, but in just over 30 years Romania-based Saint Crispin’s has managed to establish itself as one of the most revered and sought-after bespoke shoemakers on the planet thanks to grails like these. Here you have a sculptural shape fashioned from exquisitely textured leather, all shined up to see-your-own-reflection perfection.

Jack Erwin “Ellis” rubber sole Chelsea boots

Because the brand behind one of our fave penny loafers also puts out an ace Chelsea boot for a lot less coin than the whole shebang would cost almost anywhere else.

Morjas brown leather Chelsea boots

Goodyear-welted, handcrafted boots that cost way less than they should.

Cheaney “Godwin” Chelsea boots

Hard to argue with old-fashioned calf leather and oak bark-tanned soles.

Dr. Martens 2976 smooth leather Chelsea boots

What do you get when you swap out Dr. Martens’ signature yellow stitching in favor of black? A classic pair of hard-wearing Chelsea boots that welcome scuffs and scratches with relish.

Allen Edmonds “Liverpool” leather Chelsea boots

The stacked heel and almond toe gets us each and every time.

Church’s leather ankle-length boots

Wear ’em to church or on a raucous night out—saint or sinner, you’re going to look dapper-as-hell.

Our Legacy “Camion” square-toe leather boots

The shiny, not-quite patent finish on Our Legacy’s squared-off Camion boots make ’em one of our favorites, time and time again. Plus, the sturdy Vibram soles ensure you’ll never be caught slipping. 

Toga Virilis SSENSE exclusive Chelsa boots

If you want to dip your toes into the Western waters without diving into a pair of chaps, Toga Virilis’ Chelsea boots are a great middle ground.

Acne Studios leather boots

Very rarely does a shoe literally make us drool. So wipe your mouth, and then pull the trigger on Acne’s eye-candy of a Chelsea boot.

John Lobb “Kensington” leather Chelsea boots

Tips as sharp as the guy who wears them.

Andersson Bell “Fintonia” Chelsea boots

Not all Chelseas are hard angles and sharp toe boxes. Andersson Bell’s Fintonia boot is a more relaxed take that doesn’t compromise on the silhouette’s refinement. 

Prada brushed leather Chelsea boots

Congrats (or sorry): you’re now a newly-minted Prada Guy, too. 

Vagabond “Percy” suede Chelsea boot

Sometimes, a little bit of suede (especially in a dark shade of chestnut) is all you really need to take a shoe from finishing touch to fit-maker in and of itself. 

Hunter “Commando” Chelsea boots

The muck-busting Chelsea boots you’ll depend on when the forecast is just an angry face emoji.

Frye “Conway” Chelsea boots

Squared-off toe boxes are no longer a dealbreaker—so long as they’re attached to a quality pair of boots and not the weirdly shiny lace-ups that came with your rental tux.

Beckett Simonon “Bolton” Chelsea boots

It’s hard enough to find an affordable Chelsea boot that could go toe to toe with its designer counterparts, let alone one made out of full-grain calfskin sourced straight from Italy. But the footwear upstarts at Beckett Simonon pull it off with style to spare.