The Best Chelsea Boots 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.) 

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? The more tapered the toe, the dressier the shoe. Which means you’re going to want something that’s neither severely pointy nor clown-shoe huge. The ideal shape should look sort of like the top of an egg: round but not too round. And thanks to the sheer popularity of the silhouette, chances are there’s a great pair of Chelsea boots out there for you at this very moment. 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. 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 almost 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 leather 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 No-Frills 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 staffer 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

If this isn’t your first Chelsea boot rodeo, consider Common Projects. CP, of course, is the white-hot 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 no less than Kanye West 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 All-Purpose Chelsea Boot

These Chelsea boots bridge the gap between dressy and casual better than any other on this list. R.M. Williams’ Gardener boots are well-suited for putting under a, uh, suit when you mean business, and under tried-and-true denim for your more outdoorsy activities (and by outdoorsy we mean anything from attending a barn wedding to buying groceries). 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.

The Really, Really, Really Rich Guy Chelsea 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. The reason behind its relatively rapid rise in stature among the geekiest of menswear geeks? Grails like these, with a sculptural shape fashioned from exquisitely textured leather, all shined up to see-your-own-reflection perfection.

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 in between, like this duck boot-inspired riff from the Italian footwear maestros at Diemme. Those luxe suede 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 Gussied-Up Chelsea Boot

Love your wingtips but hate the hassle of lacing them up? Boy, have we got the shoe for you. These dandified Chelsea boots from Tricker’s—the storied English shoe brand founded in 1829—are made the old-fashioned way in the label’s Northampton factory with the same attention to detail that defines your poshest dress shoes. Thanks to that pedigreed made-in-the-UK construction (to say nothing of those sturdy, Goodyear-welted rubber soles) they’re the perfect complement to a rakish fall suit à la the menswear monarch himself—or just a leather jacket and your favorite pair of jeans.

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

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.

The Extendo Chelsea Boot

Over a handful of years, Bottega Veneta’s tire boots have become a label signature, selling out with the quickness each time a new version drops. Black on black is the perennially safe bet, but for our money (all $1,000+ of it) the extended-top black and brown option is the most emblematic of Daniel Lee’s short-lived tenure at the brand. If you’re looking for the Chelsea boot of the moment, these are them—near-unanimously adored by those with a penchant for high-fashion flexing and die-hard fans of the label’s premium leather goods alike.

The No-Nonsense Chelsea Boot

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.

19 More Chelsea Boots We Love