The best Chelsea boots for men are trend-proof in a way that'll make you breathe a sigh of relief. Especially right now, when menswear feels like a WWE Royal Rumble, where anything goes and trends pile up like bodies in and out of the ring. But there, floating confidently above everything, is the trustworthy Chelsea boot.
If we had to make an educated guess as to why the Chelsea boot has stuck around for so long? Good design is good design. The slip-on simplicity, the sharp silhouette, the unadorned, uncomplicated details—the pared-back design makes it highly adaptable to any wardrobe and occasion, trends be damned. So don't be ashamed to cash in on a fleeting fad, but when it comes time for you to do some spring cleaning, we'd advise against letting go of a pair of Chelseas.
We've rounded up 15 of the best Chelsea boots out there, from hardwearing stompers to exquisite stunners, under-$200 steals to $1,500 beauties. Finding the perfect pair can be hard—but pulling them on? Easy.
The Best Men's Chelsea Boots, According to GQ
Best Chelsea Boots Overall: R.M. Williams Heritage Craftsman Leather Chelsea Boots
Ask us what Chelsea boot you should get, regardless of price, and we'll point to the R.M. Williams Turnout boot, because it does so many things right that the competition can't. Off the bat, it’s a real stunner. The silhouette is sleek and chiseled, timeless and fashion forward. The leather is perfectly suited for a shine and polish to attend any black tie event, but takes on a handsome patina when worn hard. Plus, the quality is fantastic. The wholecut leather uppers are shaped as a single piece of cowhide rather than several panels stitched together, resulting in a shoe that’s as pretty as it is durable. With Goodyear-welted construction for easy peasy resoling, you’ll have these Aussie-born boots for well over a decade.
How does a boot originally built for Down Under cowboys manage to be the best-looking dress boot and hardest-wearing boot at the same time? Hard to say. The only drawback of the R.M. Williams Heritage Craftsman Chelsea is the price. But considering everything it can do—and how long it'll last—the math makes sense.
| Material | Leather |
| Sole | Goodyear-welted leather |
| Colors | Black, brown |
| Sizes | 7-16 |
Best Budget Chelsea Boots: Beckett Simonon Bolton Chelsea Boots
For the budget conscious/the dude looking for his first pair of “nice” Chelsea boots, my answer is easy: Beckett Simonon. Menswear bros might scoff at a web-only DTC clothing brand, but unlike the other brands with infinite marketing budgets looking to “disrupt the entire industry”, Beckett Simonon seems content with making great shoes at a great price, without all the soulless millennial pandering. The Bolton, a slick sleek, true-to-form Chelsea boot, is just the poster child for the brand’s modus operandi. It uses full-grain Italian calfskin, which is lined with Vachetta leather, stitched by master shoemakers in Columbia using a Blake stitch construction.
In other words, it’s a Chelsea boot with A-list looks, Northamptonshire-style pedigree, and a price that’s at least half of the competition. But if there’s one thing that will stop most people from buying a pair immediately is, well, you can’t get them immediately. Each pair is made to order, which means you’ll have to wait a month or two to get yours. But you know what they say: patience is a virtue.
| Material | Full-Grain Leather |
| Sole | Blake-stitched leather |
| Colors | 4 |
| Sizes | 7-14 |
Best All-Weather Chelsea Boots: Blundstone 500 Chelsea Boots
Some Chelsea boots lean heavily into their rockstar appeal, while others skew utilitarian, expressly designed to protect you from the elements. Then there, however, are the rare pairs that gracefully straddle the line between. Enter the other Australian boot: 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.
Tired Bushwick memes aside, Blunnies are truly good looking boots built like a tank. They can take a real whooping and still show up for their 5 a.m. shift behind the espresso machine, ready for more. They’re a boot you don’t have to feel precious about, and the de facto kicks to wear when the weather forecast just says “shitty.” They look great with vintage jeans, a pair of Dickies, cargo pants, and chinos—though, in our humble opinion, they don't belong anywhere with a dress code (explicit or implied).
| Material | Leather |
| Sole | Glued polyurethane |
| Colors | 5 |
| Sizes | 4-14 |
Best Chelsea Boots for Fashion Guys: Saint Laurent Wyatt Chelsea Boots
Hedi Slimane’s legacy at Saint Laurent was all skinny jeans, razor-sharp suits, and rockstar Chelsea boots. The look he cooked up over a decade ago has come back again, with guys dubbing themselves Hedi Boys looking to recreate the magic. One glance at boots like these, and you understand why. A leading man gleam and a stacked Cuban heel mean these boots by themselves could headline Coachella. The only update: a very right-now edginess (literally) at the toe. Whether or not the rumored skinny jeans comeback arrives, these are the boots to wear when you want all eyes on you.
| Material | Leather |
| Sole | Leather |
| Colors | Black |
| Sizes | 41-46 (EU) |
Best Chelsea Boots for All-Day Comfort: Astorflex Bitflex Chelsea Boots
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 pants. Plus, the cushioned crepe sole plays down the dressy factor while adding a ton of comfort straight out of the box.
Unlike other crepe-soled boots more famous than these—ahem—these don’t feel suspiciously soft, despite their extremely comfortable feel. In my experience, Astorflex boots maintain great arch support and mold to your feet, but also are built up enough to provide some noticeable ankle support. This is certainly the most casual Chelsea boot here, so don’t even think of trying to wear these to your friend’s wedding. You’re not “doing something”, you’re being disrespectful.
| Material | Vegetable-tanned leather |
| Sole | Crepe rubber |
| Colors | Black, stone, dark chestnut, tan |
| Sizes | 7-15 |
Best Lug-Sole Chelsea Boots: Red Wing 3192 Suede Chelsea Boots
If you think of Red Wing, it's the brand’s iconic 6-inch moc toe boots you’re probably imagining. But the Minnesotan boot makers can do more than turn out jobsite-endorsed footwear. Introduced in the 1990s, Red Wing’s Chelseas were made for ranchers who wanted something durable enough for the farm, but easy enough to nap in. They’re a happy middle ground between a high-shine European Chelsea like the R.M. Williams and the woodsy Blundstones.
That means you get Goodyear-welted construction and built-to-stroll rubber outsoles topped by Hawthorne Muleskinner roughout suede. The texture is “rugged handyman,” but the dusty tan and dark brown color can hold down a coffee date-worthy fit. White tees and white jeans? Sure. Nice pants and a knit sweater or polo? Absolutely. Wranglers and a Stetson. Of course.
| Material | Roughout suede |
| Sole | Goodyear-welted rubber |
| Colors | Tan |
| Sizes | 6-11 (UK) |
Best Suede Chelsea Boots: Morjas The Chelsea Boot
Morjas is best known for loafers worn by everyone from Wall Street bros to Greenpoint baristas. Now the Swedish shoemakers are coming for your ankles with a Chelsea boot. If you’ve already graduated from Chelsea Boots 101 by having a classic black or brown calf-leather pair in your closet, consider these brown suede beauties for next semester.
They're fully leather-lined but require absolutely zero break-in time, thanks to a studded rubber sole that feels like walking on a cloud... if clouds had traction. Style-wise, they walk the line (pun intended) between office-ready and weekend cool—equally dialed in when paired with a crisp white dress shirt beneath unforgiving Monday-morning fluorescents or some linen pants while you sip a doppia espresso in Florence.
| Material | Suede |
| Sole | Goodyear-welted rubber |
| Colors | Brown suede, black suede |
| Sizes | 5.5-13.5 |
More Chelsea Boots We Love
Dr. Martens
2976 Leather Chelsea Boots
You already know what that yellow stitching means. Dr. Martens’ chunky, iconic boots bring an EVA insole and the brand's patented oil- and slip-resistant AirWair sole to the water-resistant oiled leather. Add a pull tab for easy entry, and the only thing easier than slipping them on is adding them to cart when you realize they’re on sale.
Meermin
101050 Chelsea Boots
By cutting out the middleman and selling direct-to-consumer, Meermin offers handsome, Goodyear-welted dress shoes—all made from leather with absurdly tony provenances—for well below what the other guys charge. You can’t go wrong with any of the brand’s boots, but a mocha-hued suede Chelsea looks especially killer in the fall.
Camper
Dean Chelsea Boots
The Spanish shoe-whisperers at Camper fly a little under the radar compared to their British counterparts, but their Chelsea boots offer just as much swaggering rock-god energy as any other pair on this list. Thanks to a cushy OrthoLite footbed, though, you can wear ‘em long after Mick Jagger takes his final bow.
Our Legacy
Camion Boots
The chatter about Our Legacy's Camion boots never seems to end. That handsome silhouette, the '90s-esque square toe, and the slick side zip make these a modern-day classic.
Viberg
Antique Waxy Commander Chelsea Boots
Viberg makes boots on steroids in its family-owned Canadian factory, turning out museum-worthy footwear designed to stomp through the worst the world—or the ground, at least—has to offer. These Chelseas are cut from a single piece of waxed leather, like a Barbour jacket for your feet. Sure, plenty of other brands deploy a Goodywear welt to keep water out…but how many are putting tiny scallops into the welt just to show off?
3Sixteen
Lug Chelsea Boot
NYC-based 3sixteen has been on an absolute footwear tear lately—first with its slick Saucony collab, and now with a lug-soled Chelsea boot that stands on business. The whole shoe smashes together slightly disparate details—an elegant tobacco-colored suede, a workmanlike wedge lugged sole, an skyscraper-height ankle—that add up to something fresh in the normally staid world of Chelsea boots. And if you’ve ever broken in a pair of 3sixteen’s top-tier jeans, you already know: things only get better as you put in the steps.
How to Style Chelsea Boots
Chelsea boots have always looked cool—anywhere, on anyone, at any time. They were invented in the 1800s, but won their cultural cred later: the Beatles gave them a massive co-sign in the ’60s, then Hedi Slimane anchored his Saint Laurent rocker suits with them while rappers stacked their denim on top of Chelsea boots during the 2010s.
Which goes to show that Chelsea boots work with damn near anything in your closet, from your favorite Levi’s to baggy chinos to louche suits—even crew socks and shorts, depending on the boots and your taste for channeling some Pacific Northwest crunchiness. For more, check out our guide on how to wear Chelsea boots.
How We Test and Review Products
Style is subjective, we know—that’s the fun of it. But we’re serious about helping our audience get dressed. Whether it’s the best white sneakers, the flyest affordable suits, or the need-to-know menswear drops of the week, GQ Recommends’ perspective is built on years of hands-on experience, an insider awareness of what’s in and what’s next, and a mission to find the best version of everything out there, at every price point.
Our staffers aren’t able to try on every single piece of clothing you read about on GQ.com (fashion moves fast these days), but we have an intimate knowledge of each brand’s strengths and know the hallmarks of quality clothing—from materials and sourcing, to craftsmanship, to sustainability efforts that aren’t just greenwashing. GQ Recommends heavily emphasizes our own editorial experience with those brands, how they make their clothes, and how those clothes have been reviewed by customers. Bottom line: GQ wouldn’t tell you to wear it if we wouldn’t.
How We Make These Picks
We make every effort to cast as wide of a net as possible, with an eye on identifying the best options across three key categories: quality, fit, and price.
To kick off the process, we enlist the GQ Recommends braintrust to vote on our contenders. Some of the folks involved have worked in retail, slinging clothes to the masses; others have toiled for small-batch menswear labels; all spend way too much time thinking about what hangs in their closets.
We lean on that collective experience to guide our search, culling a mix of household names, indie favorites, and the artisanal imprints on the bleeding-edge of the genre. Then we narrow down the assortment to the picks that scored the highest across quality, fit, and price.
Across the majority of our buying guides, our team boasts firsthand experience with the bulk of our selects, but a handful are totally new to us. So after several months of intense debate, we tally the votes, collate the anecdotal evidence, and emerge with a list of what we believe to be the absolute best of the category right now, from the tried-and-true stalwarts to the modern disruptors, the affordable beaters to the wildly expensive (but wildly worth-it) designer riffs.
Whatever your preferences, whatever your style, there's bound to be a superlative version on this list for you. (Read more about GQ's testing process here.)
