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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.
The Best Chelsea Boots, According to GQ
- The Era-Defining Pick: Saint Laurent "Wyatt" Chelsea boots, $1025
- The Bang-for-Your-Buck-Pick: Beckett Simonon “Easton” Side-Zip Boots, $259
- The Shockingly Comfortable Pick: Astorflex Bitflex Chelsea Boots, $250
- The Crappy Weather Pick: Bludstone 500 Chelsea boots, $210
- The Rough-and-Tough Pick: Red Wing Heritage Classic Chelsea Boots, $300
- The All-Purpose Pick: R.M. Williams “Gardener” Chelsea boots, $530
- The No-Frills Pick: Morjas brown leather Chelsea boots, $399
- The Caballero Pick: Unmarked El Torino Boots, $390
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.)
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 2024 turns out to be the decadent return to form it's shaping up to be, we wouldn't count the shoe that can easily cross over from work boot to dress shoe out just 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 Best Chelsea Boots, Period: Saint Laurent Wyatt Chelsea Boot
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 Best Bang-for-Your-Buck Chelsea Boots: Beckett Simonon Preston Chelsea Boot
In 2023, it’s tough to swing a branded tote without hitting a byproduct of the first DTC wave, a torrent of cheerily inoffensive disruptors dead-set on upending the way we shop, sleep, and brush our teeth. Beckett Simonon shares a lot in common with its counterparts from that era—the online-only brand got its start on Kickstarter in 2011—but its mission actually feels a little radical: high-quality, handmade dress shoes at prices that don’t require a second mortgage. The Easton, a slick side-zip riff on a classic Chelsea boot silhouette, might be the best representation of its MO. The full-grain calfskin is sourced from Arzignano, Italy, then shipped to Colombia, where it’s equipped with a Vachetta leather lining and finished with Blake stitching, a whole lot of old-school craftsmanship for a relatively meager $260. If all that jargon means squat to you, just take a look at that subtle almond-shaped toe box: you won’t find a silhouette that dialed for less money, no matter how much time you spend wandering the factories in Northampton.
The Most Comfortable Chelsea Boots: Astorflex Bitflex Chelsea Boot
Astorflex has long been one of the best value propositions in the shoe space. The Tuscan vegetable-tanned leather and multigenerational craftsmanship alone should be worth more than what you'll actually pay. But value doesn't equate to style. Thankfully, the Bitflex has that in spades. Not too pointy and not totally bulbous, the shape splits the difference masterfully and looks great paired with any kind of pant. Plus, the cushioned crepe sole plays down the dressy factor while adding a ton of comfort straight out of the box.
The Best Crappy Weather Chelsea Boots: Blundstone 500 Chelsea Boot
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 Best Work-Ready Chelsea Boots: Red Wing Classic Chelsea Boot
Oh, you need some chelsea boots to actually get some shit done? Red Wing, baby! The Minnesota-based brand has been pumping out some of the hardest-wearing bomb-proof boots for over a hundred years and they're not too bad to look at, either. They've been the boot of choice for generations of tradespeople, leagues of stylish dudes, and scores of discerningly fashionable celebs. The heritage brand's Classic Chelsea Boot uses their famously beefy leather which Red Wing tans in-house and is built with a supportive shank, foot-moulding cork fill, and a grippy, spongey Vibram sole. On top of that, once you eventually wear through them, you can easily have them resoled. The reward for good work is more work!
The Best All-Purpose Chelsea Boots: R.M. Williams Gardener Boot
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 Best No-Frills Chelsea Boots: Morjas Chelsea Boot
The next-generation hard-bottom evangelists at Morjas craft their Chelsea boots from smooth calfskin leather, ditching the extraneous flourishes in favor of a slightly wider toe box for added comfort. The just-slight-enough stacked heel and grippy rubber sole ensure you won't be slipping around should the weather take a turn for the worst, but the real X factor hear is their ability to straddle the dressy-casual divide with grace—like the R.M. Williams joints above, their sleek vamp means they'll look right at home with any trousers you pair 'em with. And when it comes to Chelsea boots, what more can you really ask for?
The Best Cowboy-Inspired Chelsea Boots: Unmarked El Torino Boot
If you're feeling a little yeehaw down in your boots, but the traditional Chelsea boot ain't scratching that itch, you should look to the traditional Mexican style known as a charro boot, or botines de charros. Like a Chelsea boot, charro boots have an ankle height and elastic side gores. But the big difference is the distinctive leather detailing that covers the elastic panels which give the boot a rugged elegance befitting of the most suave caballero. Unmarked's El Torino boots are among the best and come with all the trappings of an artisanal boot including high-quality leather, Goodyear-welted construction, and, true to cowboy form, lemonwood pegs.
Plus 5 More Chelsea Boots We Love
