Tested: The Best Men’s Chelsea Boots for Any Occasion

Popularized by Englishmen (and women) throughout the ’60s, the Chelsea boot makes for a silhouette that has surely stood the test of time. While they grew popular throughout Great Britain (and later around the globe), the boot’s name is a product of its environment, as Chelsea was and still is one of London’s trendiest neighborhoods. For further confirmation of their popularity, the most famous Brits at the time had a strikingly similar style of boots made in their name; here’s a hint: they start with “B” and end with “eatle Boots.” Nowadays, Chelsea boots have transcended into an immensely common piece of footwear — one we think should be in every man’s wardrobe. With countless budget options and knock-offs in the mix, it could be impossible to narrow down exactly which brand is right to choose — but we’ve gone ahead and made it easy for you by getting hands-on with some of the best men’s Chelsea boots.

How We Tested

We’re back in action with another hands-on entry into our Tested series, where we take a closer look at some of our favorite gear and apparel across the board. Today, we’re focused on the iconic Chelsea Boot, a true wardrobe essential with British roots and a whole lot of style. Of course, we made sure to hand-select only the best of the best from brands that we can depend on, after extensive online research and collaborating with colleagues.

As we do with all of our style tests, our process begins by inspecting each pair of boots off the foot, taking note of the build quality, material quality (in this case, leather), and anything that stands out. Next, we get to work trying everything on, paying attention to how everything fits and feels right off the bat. Of course, we walk around in each pair to gauge the fit (and how easy they were to put on and take off) even more while putting the traction to the test to see if it’s suitable for day-to-day wearing (and even wearing on rainy days). Finally, we’ll talk a bit about the style of each pair of boots, as there’s plenty to choose from, like the Western-inspired Tecovas or the classic Clarks boots.

Measurements: I’m 6’2″ and wear a size 10.5/11 shoe. Although I’m a half-size, I usually go with an 11 when it comes to things like boots, especially with Chelseas, which are usually a bit more snug by nature.

What to Look For

Material: Most people want their boots to be able to stand up to tough conditions. But since Chelsea boots have more of a fashion slant, leather and suede are popular materials. This doesn’t mean they can’t be durable and taken out into rougher terrain, but they’re generally preferred for style over function. That’s why it’s important to decide if you’d like some water protection on your boots, which you can do yourself if they don’t come with that.

Design: Chelsea boots have an iconic silhouette, characterized by being low to the ground, just above the ankle, and having a tab (or two) to maneuver them. But different labels will shake things up here and there, taking inspiration from ranch boots or work boots, for example. Elastic, or some kind of stretchy fabric on the side of the boot, is also a key ingredient for the iconic look (and to make them easy to put on and take off).

Fit: Chelsea boots should be snug enough to keep the ankles from jostling around/riding up your legs, but not so snug that you’re feeling suffocated. This can be hard to pin down, especially since many of them require a break-in period, but if you have wider/bigger feet like myself, I recommend going for a half size up to be safe.

Clarks Clarksdale Easy

Best Starter Boots: Clarks is a true heritage brand that has two centuries of craftsmanship under its belt, which means any good boots guide should at least give them a shout-out. For our Chelsea boots guide, we went with the label’s Clarksdale Easy boots, a faithful take on the absolutely timeless style.

The Good

Clarks and boots have been walking hand in hand for nearly 200 years, so it’s safe to say that the British heritage brand knows a thing or two about building a good one. While they may be best known for their Desert Boot (which we covered over on our guide to the best chukka boots), the rest of the label’s offerings are just as impressive, like the Clarksdale Easy boots, for example. This boot starts with a beeswax leather upper that’s soft to the touch, and it sits on top of a classic natural crepe outsole with a rubber heel top piece. Inside, you’re getting a leather-lined Contour Cushion insole that feels very supportive (and not too rigid, which is appreciated as these require a bit of a break-in period; more on that later), and it’s finished with elastic inserts on the side for easy on and off, along with a premium leather storm welt. The crepe outsole gives you some pretty solid traction, but I wouldn’t recommend using them to walk in the rain if you can help it. The look of these boots is just absolutely classic, too, with a very clean style that stays true to the classic Chelsea construction. 

The Not So Good

Fit here runs a tad small, but as you break them in, this shouldn’t be a problem (I do recommend wearing thicker socks as you’re doing this to avoid any pain around the ankles, though). The toe box is also a bit on the tighter side, but again, this should open up over time and form to your feet. 

Verdict

Hailing from an absolute legend in the footwear industry, this pick from Clarks is the perfect starting point for anyone who doesn’t own a pair of Chelseas, or anyone who just wants a reliable and classic pair of boots that will always look good. 

Dr. Martens 2976 Nappa Leather Chelsea Boots

Best Classic Boots: Though their backstory is polarizing, Doc Martens has been embraced by countless counter-cultures over the past five decades. Docs are pragmatically the Converse of boots, and the 2976 silhouette is the quintessential Chelsea boot, providing that classic ’70s look that never goes out of style. More or less, everything else is as expected, right down to the Goodyear Welted leather construction, and what you see is what you get with a brand as renowned within their circle as Doc Martens. After all, he’s a doctor.

The Good

Back in the ‘60s, Chelsea boots became a symbol of counter-culture and the mod scene as a whole (think The Beatles and The Stones), and with Dr. Martens’ expansion into the UK, the label boots adorned the feet of punks, new wave artists, and the youth at large by the ‘70s. To this day, that yellow stitching is about as iconic as you can get, and the label’s 2976 Nappa Leather Chelsea Boots are just oozing with that ‘70s vibe. Built using a lightweight, milled Napa leather up top that feels buttery smooth, you’re getting a trusted pair of boots that boast Goodyear-welted lines that have been heat-sealed at 700°C and reinforced with the label’s signature welt stitch. The fit here is true to size, and they felt surprisingly broken in even out of the box (although the toe box will take some time to open up). Putting these on and taking them off was also super easy, too, helped by the iconic pull tabs on the heels. Traction is also super solid here, thanks to the label’s signature grooved outsole, adding to that classic style as well. 

The Not So Good

The only downside with these boots is that they don’t come in half sizes, which can be a bit of an issue if you’re in between sizes. I myself wear a 10.5, so I went with an 11 here, which felt perfect, so I recommend going a half size up from your usual foot size if you’re in between sizes.

Verdict

As some of the most iconic boots in the space, Dr. Martens’ classically ‘70s Chelseas remain some of the most recognizable boots and are built to last.

Thursday Boots Cavalier

The Safe Pick: The qualifications that land a boot a spot on this list can be dubbed “The 3 Cs” and read as follows: Comfy, classy, and Chelsea. Oh, make that 4: Cavalier. While all of Thursday Boots’ options are worth a look, the Dusty Brown Suede colorway makes for a sustainably stylish couple of stompers from a brand admittedly willing to fight the big industry prices. Thursday’s Cavalier Boots make for a great pair on every day of the week and are built for your busiest days, as the New York-bred brand might know about being busy better than anyone else.

The Good

With a name like Thursday Boots, you better believe that the label is dedicated to crafting no-nonsense boots that use high-quality materials (and don’t break the bank). For our Chelsea boots guide, we’re taking a look at the label’s Cavalier silhouette, which opts for a suede upper and Goodyear welt construction to ensure they’re built to last. Inside, you’re getting a fully lined glove leather interior that feels super comfortable, along with shock-absorbing insoles and a cork-bed insole that will form to your feet over time. Finally, the boots are finished with a leather outsole that features these TPU studs that help a lot with traction (I tested these both inside and outside the office, and other boots can sometimes cause me to sleep while walking on smooth concrete; these definitely didn’t), and of course, elastic goring on the ankles and Goodyear welting. Fit here is true to size, but the shoes run a bit narrow, which I’ll get into below.

The Not So Good

My only gripe, and admittedly a personal one, is that the boots are a bit on the pointier side, and taper towards the toe box, which results in a more narrow fit (and a dressier look) compared to other boots. It never felt constricting, but if you have wider feet, then you may want to go for a half-size up. Also, the lack of pull tabs on the heel does make putting them on and taking them off slightly harder, but it adds to the clean look, and I didn’t find my self struggling that much more. 

Verdict

Clean, simple, and high-quality, you can trust that you’re getting simple yet reliable boots whenever you go with Thursday, and these Chelsea are no exception. 

Blundstone #510 Chelsea Boots

Best Outdoor Boots: As an O.G. within their industry, Blundstone has surely progressed with the times, putting forth a pretty stylish boot that you won’t worry about dirtying up. As a matter of fact, they’re crafted with the expectation of getting a little messy. With many models to choose from, few match the stylistic simplicity of their classic 510, providing a stable, long-lasting boot built for harsh weather that can provide you with grit and glitz altogether.

The Good

Perhaps the most popular Chelsea boots at the moment come from the Australian brand Blundstone, and the hottest silhouette that they offer is no doubt the #510 (best recognized by the iconic pull tabs on the front and back of the ankles). But don’t let the ubiquity of these shoes turn you off, as they’re easily the most comfortable Chelseas in the guide, and fit me perfectly right out of the box. I’ll expand on the fit and feeling more, but let’s start with the construction: you’re getting a water-resistant leather upper with elastic sides and those iconic pull tabs (denoting the brand and its home state of Tasmania, Australia), supported by a cushioned midsole for reliable comfort and a TPU outsole that has deep grooves for plenty of traction (some of the best in this list, by the way). You’re also getting the label’s SPS Max Comfort system for shock absorption (which is very much appreciated if you’re wearing these for an entire work day, especially if that means a lot of walking around), along with a steel shank for added stability. 

The Not So Good

Even though these do require a bit of a break-in period (as most good boots do), I really feel like these are the most comfortable Chelsea boots in the game right now, and are super easy to take on and off. This easy-wearing is bolstered by the super versatile look here, making these a great all-arounder pick, as well as a solid outdoor choice thanks to the traction provided by the outsole and the water-resistant leather.

Verdict

You’ve seen them everywhere (and you’ve probably heard people raving about them just as I did above), but don’t let that discourage you from hopping on the hype train. Blundstone’s #510 Chelseas are some of the most comfortable boots on the market right now, and continue to dominate the scene for good reason. 

Danner Bull Run Chelsea

Best Work Boots: “Made for wear and tear” and “Made in the USA” are a pair of phrases that have grown synonymous at this point; luckily, Danner is one of many brands that distinguish the difference between synonymous and monotonous. With stitch-down construction for durability’s sake, the Portland-based Bull Run offers immense traction and easy on/off, making them yet another great addition to Danner’s broad selection of rugged footwear.

The Good

Danner may be better known for its outdoor gear and workwear (which Chelsea boots usually don’t fall under the category of), so you might be surprised to learn that the label’s Bull Run Chelsea boots are super impressive even if you’re not using them for work. Made in the States with care, these boots start with a full-grain, oiled leather upper for some added water resistance, and boast electrical hazard protection for even more utility. On the bottom, you get a removable Ortholite insole working with Danner’s in-house Wedge outsole, which is made for long-lasting comfort on smooth indoor surfaces (think concrete and wood), and it’s finished with a stitchdown construction. These were super easy to put on and take off, and have a noticeable heft to them, which is ideal for work boots. The leather feels very smooth, and you’re getting thick heels that sort of taper towards the toe with a slip-resistant outsole that’s super convenient.

The Not So Good

The beefy outsole here adds to the weight and makes these considerably heftier than other picks in the guide, but I wouldn’t necessarily consider this a downside, especially if you plan on doing any manual labor in these. 

Verdict

Made for work and reinforced with electrical hazard protection, these are the perfect Chelseas for working men who want to inject a bit of style into their wardrobe without sacrificing utility. 

Tecvoas The Chance

Best Western Boots: Marrying the best of the Chelsea boot’s style and function with a western slant (specifically Texas), The Chance from Tecovas is a versatile urban boot. Designed in Austin, Texas, and made in Leon, Mexico, these boots have the classic Chelsea silhouette with a western-inspired leather sole, and Goodyear welt construction. These boots fit right in with a pair of jeans, whether they’re for the ranch or for the city.

The Good

These have a similar style to Thursday Boots’ Cavalier silhouette, but take the Western look to the next level with a Chelsea style sitting on a Western platform. They’re made with Bovine leather (which is commonly used in dress shoes) and boast a ¾ Goodyear welt construction with a classic round toe. Of course, the silhouette was inspired by Western style, but Tecovas is injecting some city-friendly look here as well for more versatility. You’re getting a super clean and formal look that’s perfect for nights out or elevating an outfit, and the Bovine leather here also just feels (and looks) super high-quality. I also really liked the lowkey heel tab that doesn’t go above the heel, as it keeps the silhouette looking minimalist and dressy. The insole is also solid here, but not quite as supportive as something like Blundstone’s.

The Not So Good

These don’t have the best traction, but they’re meant for more casual/formal settings and not meant to be work boots like Danner or Red Wing boots. It can also take some getting used to the 6” heels here if you’re not used to wearing them, but I didn’t find it to be too hard (even as someone who doesn’t often wear shoes with heels). 

Verdict

Blending classic Western style with city-friendly looks (and supple Bovine leather), Tecovas’ The Chance boots are the perfect dress boots for anyone who wants to channel their inner cowboy.

Red Wing Heritage Classic Chelsea

Best All-Arounders: Red Wing is perhaps better known for its workwear, but the label’s casual offerings blend the label’s renowned durability with every day style, just like these Chelsea boots do. You’re getting a blend of Red Wing’s renowned build quality with classic Chelsea boot styling, so you can trust that these are built to last.

The Good

Hailing from an absolute legend in the workwear space, these boots are similar in a lot of ways to Danner’s Chelsea boots, with a beefy construction and a flatter outsole without a heel. Made in the States with care, they start with a full-grain (and oiled) leather upper that sits on top of a fully cushioned insole that will only get softer. There’s a single pull tab on the heel for easy wearing, along with those classic elastic sides, and it’s finished with a Traction Tred outsole (which gives you really solid traction on smoother surfaces like concrete, which is where we tested) and Goodyear welted construction. The bump toe is a nice touch as it gives your toes more room, and these have a more classic Chelsea look compared to other workwear-inspired picks like Danner’s boots. I’ll expand on how easy these were to take off and put on below (hint: it’s a little hard), but once they were on, the fit felt true to size and comfortable.

The Not So Good

Like other red wing shoes, these look and feel pretty beefy, and will take some time to break in before they feel super comfortable (I noticed they were pretty tight around the toes), but after that, you’ll have some of the longest-lasting boots you can get. I also found these a bit harder to put on compared to other picks, but it wasn’t that big of a struggle and should get better as they break in. 

Verdict

Red Wing’s workwear experience translates into a casual yet rugged pair of Chelseas that look absolutely classic. They’re made in the States with care and will last for the rest of your life with proper care.

Chelsea Boot Comparison chart

What Exactly Is A Chelsea Boot?

For the uninitiated, Chelsea boots are a close-fitting ankle boot outfitted with with stretchy, elastic side panels. You’ll also notice that many of these boots feature a fabric or finger loop at the both the front and back to easily pull them on and off.

The goal is to create a sophisticated boot that can be dressed up or dressed down depending on the occasion. They’re also incredibly popular in the workwear scene, found on the feet of mechanics in service shops everywhere due to the lack of laces, protection, and  oil+slip resistant outsoles found on many options.

Chelsea Boot History

The Chelsea boot’s origins date back to the Victorian era, around the mid-1800s, and legend has it that Joseph Sparkes-Hall (a renowned bootmaker from London) created them with the goal of blending comfort with style (with the first pair going to Queen Elizabeth, who was famously a big fan of the shoes). Fast forward to the ‘60s, when the Chelsea boot gets adopted by the mod scene and embraced by absolute legends like The Beatles and The Rolling Stones, cementing themselves as icons in fashion history.

Today, this timeless footwear staple continues to reign supreme, seamlessly transitioning from casual outings to formal affairs with its signature elastic side panels and sleek silhouette. While the overall look and style of Chelsea boots are still mostly rooted in tradition, a lot of modern takes come in a variety of styles, materials, and heel variations, but still remain a must-have in every man’s wardrobe.

Honorable Mentions

Tired of getting your Achilles heel gnawed at while trying to break in a new pair of boots? Look no further, as these are practically like a pair of Vans, giving wearers virtually no trouble when walking into that one friend’s place who is way too uptight about their carpet. Beckett Simonon’s Bolton Boots are made out of pure calfskin, worth every penny, and, surprisingly, don’t cost a baffling amount of them.

Common Projects is a brand that can be found along various walks of life, be it an upscale wedding or a low-key night out. Worn by rapper-turned-shoe-salesman Kanye West himself, the Common Projects Suede Chelsea Boots garner a solid stamp of approval as far as staying fashion-forward is concerned. And, just in case Ye’s name isn’t enough of a stamp, the brand’s signature series number is subtly printed in gold by the heel. Sold in a neutral tan colorway as well as chocolate brown, these almond-toed boots were hand-stitched in Italy, as goes for each of the brand’s pairs.

The Australian-bred R.M. Williams is famous for its Chelsea boots, so this should be a no-brainer. However, they do offer a variety of other quality clothing that would pair perfectly with the former. Take it as a business tactic. Founded by the man who shares its namesake, Williams was merely a swagman until ultimately growing into an esteemed name and brand. The R.M. Williams Comfort Craftsman Suede boots are meticulously crafted from Goodyear-welted leather, a couple of pull tabs, and all that good stuff for a fraction of the cost that brands who do the very same charge. Choose from a trio of colors and wear them with the coolest jeans you have.

As England’s longest-tenured shoemakers, the lads at Tricker’s have been crafting country boots since 1829, which is practically two centuries at this point. The Tricker’s Henry Country Dealer Boot evokes their start, built on their original Commando sole that was curated with the damp countryside in mind. Sold in three rustic colors, these storm-welted steppers have a dual tab for ease and were put together with nothing but some of the finest leather, as you’d expect getting this deep into the list.

With glazed calfskin, these manage to shine through rain, snow, or sleet. Akin to their denim — and catalog in its entirety — these A.P.C. Chelsea Boots are formidable, pricey, and stylish as hell. Never one to necessarily push the envelope, the Parisian off-the-rack brand keeps things elegant and direct, simple and shining. This slightly-square-toed dress Chelsea will get you through whichever black-tie event you find yourself attending next. The Charlie Boots run one size small, so make sure to take it down a notch to prevent ending up with purple feet; even then, these might still be worth it.

Tested: The Best Chinos for Men to Wear Anytime

You may want a pair of equally versatile pants to go with your new Chelseas, so head on over to our guide that covers the best chinos you can get.