Need something a little slicker and sleeker in your footwear rotation? Allow us to introduce you to the very best Chelsea boots for men. For even more autumn-ready kicks, don't miss our breakdown of all the finest fall boots to buy right now.
Over the past few years, the almighty Chelsea boot has emerged as the shoe of choice for style-minded men thanks in large part to its versatility—it’s both a stylish upgrade to sneakers and a badder-ass option than standard dress shoes. But the appeal doesn’t stop there. They’re the easiest shoes this side of pool slides to get on and off; the right ones are comfortable enough to hike around in all damn day; and they can be worn with your best spanking-new suit or your oldest threadbare jeans. And the Chelsea has a pedigree both regal and rock ‘n’ roll: The shoe is widely attributed to Queen Victoria’s bootmaker in the mid-1800s, and they picked up their name a century later when London’s Chelsea cool kids started sporting them. The Beatles were soon wearing them (with Cuban heels, no less), and then The Rolling Stones. And about a minute after that, everyone else. Even Stormtroopers wore Chelsea boots in Star Wars. Despite rock ’n’ roll music falling out of favor with the masses in the past decade, the rock ’n’ roll look (beat-up jeans, leather biker jackets, wallet chains) has never been more popular—and neither have Chelsea boots.
Chelsea boots are defined by two important details: an ankle-hitting height and an upper constructed from two pieces of leather (the front, a.k.a "vamp," and the back, a.k.a. "quarters") sewn together. The most common silhouette features a panel of elastic that joins the two parts together. Other versions feature a zipper closure—whether or not those are technically Chelsea boots is up for debate, but the look is all the same. 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. So you want something that’s neither severely pointy nor clown-shoe bulbous. The ideal looks sort of like the top of an egg: round but not too round. And thanks to the ubiquity of the silhouette (you’ll find it stocked to the ceiling at any mall, and also Los Angeles's hyper-luxe Maxfield), there’s a great pair of Chelsea boots out there for you. Whether you’ve got $100 or $1,000 to spend, or you're looking for smooth leather or velvety suede, these are our favorite wear-with-everything Chelsea boots that you can pick up right now.
The Chelsea Boot
Saint Laurent "Wyatt 30" Chelsea bootBuy Now
It was six years 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 quality 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). The “30” in the name refers to the heel height (in millimeters, which works out to a little more than an inch), which is enough of a boost to help you look striking, but not much more than any pair of dress shoes you already own. And 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
New Republic chuck suede Chelsea boot
The boot that launched a thousand fits.Buy Now
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 Man boots—sandy suede, cushy crepe sole, happy-making $99 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: They feel like walking on memory-foam pillows." Confidence-boosting, fashionable-making, pillow-walking boots for under a hundred bucks? Hard to turn that down.
The Slightly-More-Frills Chelsea Boot
Common Projects suede Chelsea bootBuy Now
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 sole—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
Church's "Prenton" suede Chelsea bootBuy Now
These Chelsea boots bridge the gap between dressy and casual better than any other on this list. Church's Prenton 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 black.
The Wildly Affordable Outside-of-the-Box Chelsea Boot
Steve Madden "Auras" Chelsea bootBuy Now
Here, the good folks at Steve Madden grabbed the best elements of high fashion and made them available—not to mention affordable—to the masses. The upper is made from real-deal leather, the toe box is perfectly chiseled, and even the harness detail (hardware that can go so tacky so quickly) is the right scale and tone for this kind of boot. The suede might feel nubbier than the hides you’ll find on more expensive pairs, but it works for this rugged twist on the classic.
The Really, Really, Really Rich Guy Chelsea Boot
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. 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 Stage-Readiest Chelsea Boot
Givenchy pointed toe ankle bootsBuy Now
Leave it to the most exciting designer in menswear to concoct a pair of Chelseas that are a little rock 'n' roll, a lot of badass, and uncommon in all the best ways.
The No-Nonsense Chelsea Boot
Jack Erwin "Ellis" rubber sole Chelsea bootBuy Now
The brand behind our go-to penny loafers also puts out an ace Chelsea boot for not a ton of money that features a slip-free rubber sole.
The Indoor-Outdoor Chelsea Boot
1017 Alyx 9SM Chelsea boot with removable Vibram soleBuy Now
Sure, your beloved Blundstones are technically an all-weather Chelsea boot. But their bulbous toe boxes and thick soles won't look quite right with your best tailored clothes. Alyx's edgy version gives you the best of both worlds: those tractor-tire Vibram soles will keep you high and dry in a downpour, and they pop right off for a trimmer, dressier look once you reach your destination.
The Runway Dupe Chelsea Boot
Aldo "Agriracien" Chelsea ankle bootBuy Now
The best part about Chelsea boots long reign of dominance? The budget brands have had ample time to step their game up. These Aldo numbers won't hold up for anywhere near as long as our fave Saint Laurent pair, but for well under $200 they're a pretty decent facsimile. Same higher rise at the ankle, same high-but-not-too-high heel, same aggressive toe shape, killer shade of almond brown suede.
The Change-Up Chelsea Boot
Thursday Boots "Rogue" Jodhpur bootBuy Now
Feeling a little bored with the basic Chelsea silhouette, but still want something sleek and slim and easy to wear? Get familiar with the Chelsea's close cousin the Jodhpur boot. It might not seem like a lot, but that single strap across the heel will freshen things up way more than you'd expect.
The Hidden Flex Chelsea Boot
Christian Louboutin "Samsocool" red sole Chelsea bootBuy Now
Buy for the details you can see, like that extra-sleek silhouette, and the one you can't: CL's famous red lacquer sole.
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