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 Shopping Guide
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 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 All-Purpose Chelsea 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 No-Frills 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 Crappy Weather 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 Chelsea Boot of the Moment
This isn’t the first time we’ve praised the Camion, Our Legacy’s platonic do-everything boot. The Scandi brand’s Cowboy-esque take on a classic Chelsea silhouette is plenty refined—see the tonal stitching and low heel—but its gently squared-off toe adds just enough edge to take your fits to the next level. Plus, the zipper entry is great for easy on/off access, a feature you’ll appreciate when it’s way too hot to bother with squeezing your foot between two elastic bands. In the past we’ve recommended wearing these boots with light-wash jeans or a razor-sharp black suit, but honestly, they’ll look good with just about anything—giant khakis, worn cargos, tweedy dress pants.
The Chelsea (by Way of Texas) Boot
Looking for a pair of Chelsea boots with a little more giddy-up energy? You’re in luck: these days, the Venn diagram of Chelseas and their yeehaw-leaning counterparts looks a lot more like a circle, and Tecovas sits squarely at the center of it. The American brand’s western-inspired zip-up boot (no side panels here) comes crafted from some of the hardiest, high quality-iest leather on the planet, and features water-resistant uppers, ranch-ready insoles, and a sturdy Vibram outsole, a primo example of the craftsmanship Texas is known for. It’ll look killer anchoring a newfangled riff on the Canadian Tuxedo, but we’re especially partial to how nicely it syncs up with a blazer and lush winter-weight cords. Go get ’em, cowboy.