To revisit this article, select My Account, then View saved stories
Find anything you save across the site in your account Mens Leather Winter Boots
Find anything you save across the site in your account
By Michella Ore and Jake Woolf
All products featured on GQ are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.
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 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.
"Wyatt" Chelsea Boots
Material: Leather, Suede Colors Available: 4 Size Range: 6-13
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.
Material: Full-Grain Leather Colors Available: 5 Size Range: 7-14
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.
"Gardener" Whole-cut Leather Chelsea Boots
Material: Leather Colors Available: 2 Size Range: 7-16
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.
Material: Leather, Suede Colors Available: 5 Size Range: 5.5-13.5
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?
Material: Leather Colors Available: 6 Size Range: 3-14
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.
"Camion" Square-toe Leather Boots
Material: Leather Colors Available: 3 Size Range: 2-14
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.
Material: Leather, Suede Colors Available: 2 Size Range: 7-15
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.
George Cleverly's sleek leather boots hit right at the ankle to ensure a snug fit without compromising easy on/off access. Clever by name, clever by nature!
If you want to enjoy all the quintessential Britishness of a classic Chelsea boot but need the durability of a rugged Vibram sole, Crockett & Jones' grained leather riff—equipped with blizzard-busting rubberized cleats—is just the shoe for you.
x Tricker's "Henry" Wing Cap Chelsea Boot
When two menswear legends love each other…they get together to whip up a very sick, very shiny brogue-boot hybrid that indicates you know when to have good time and when to get down to business.
We were today years old when we found out that adding a slightly squared-off toe to a timeless calfskin silhouette makes it look at least a quarter cooler. (Just kidding: we've known that for a while. But we're thrilled to share the official evidence with you.)
"Eternal" Cowboy Chelsea Boot
"Balbi" Chelsea Boots
"Pierrot" Leather Boots
"Godwin" Chelsea Boots
Congrats (or sorry): you're now a newly-minted Prada Guy, too.
"Conway" Chelsea Boots
The Best Boots for Men, From A to Z
The Best Loafers for Men to Crush All Your Summer Fits
The Best Chelsea Boots for Men to Wear With Everything
The Best Sandals for Men Will Make Your Summer Even Hotter
The Best Dress Shoes for Men Are More Essential Than Ever
Not a subscriber? Join GQ to receive full access to GQ.com
By Gerald Ortiz and Jake Woolf
Wayfair discount code for 15% off your entire purchase
Save extra 25% w/ Michaels coupon
Enjoy 30% Off w/ ASOS Promo Code
Take extra 20% off purchase with eBay coupon code
Grab Peacock Premium for Only $1.99/Month Instead of $5.99
$100 discount on your next Samsung purchase* in 2024
mens leather gym shoes © 2024 Condé Nast. All rights reserved. Use of this site constitutes acceptance of our User Agreement and Privacy Policy and Cookie Statement and Your California Privacy Rights. GQ may earn a portion of sales from products that are purchased through our site as part of our Affiliate Partnerships with retailers. The material on this site may not be reproduced, distributed, transmitted, cached or otherwise used, except with the prior written permission of Condé Nast. Ad Choices