10 Best Chelsea Boots for Men in 2025, Tested | Value, Comfort, & Style

Today, after hundreds of reviews and articles over some eight years of publishing, we’re giving you our list of the best Chelsea boots for casual wear, formal wear, and everything in between.

Why should you listen to this random article? Look, I know I can’t try every boot on Earth, but I’m pretty sure I’ve worn and reviewed more Chelseas than anyone else, and it’s all been documented on our YouTube channel to over 100,000 subscribers.

But because anyone can just try a bunch of boots, I’ve gone further and visited producers of boots and leather in over ten countries, from Italy to Indonesia, all in the name of figuring out what characterizes a great boot at different price points.

I break down our criteria some more below, but that “at different price points” thing is an important qualifier: just because a product isn’t the most expensive doesn’t mean it can’t be great, or that it won’t be perfect for you.

So here’s a new list of my favorite Chelsea boots.

Our Top-Picks: Best Men’s Chelsea Boots

• Best Value Chelsea: Thursday Boot Company’s Cavalier
• Best Budget Work Chelsea: Redback’s Easy Escape
• Best Waterproof Chelsea: Ariat’s Wexford
• Best Whole Cut: Meermin’s Whole Cut Line
• Best Casual Chelsea: Astorflex’s Bitflex
• Best Made-in-USA Chelsea: Red Wing’s Weekender
• Best Smart Casual Chelsea: Grant Stone’s Chelsea
• Best Rugged Chelsea: Bordon Colombia’s Isidro
• Best Dressy Chelsea: Carmina Shoemaker’s Simpson
• Most Premium Chelsea: Briselblack’s The Seventh

How and Why We Define the “Best” Chelsea Boot

No boot is harder to recommend than the Chelsea, mostly because you can’t really adjust the fit. This means there’s just a much higher likelihood of a recommendation not fitting you and through no fault of your own or the brand.

So here are some things to keep in mind as you look at our picks:

1. You can fix a too-big Chelsea for $10.

My low instep and skinny ankles have always made it hard to find the right Chelsea — until I bought tongue pads from a German company called Pedag. They didn’t sponsor this article or anything, but they helped me fit so many boots (and loafers) that were previously off limits to me. You stick them under your instep and voilà: Chelseas fit.

2. Great Chelseas should try really hard to fit you.

In a similar Chelseas-are-hard-to-size vein, the list emphasizes options that offer half sizes, wide sizes, quick delivery, and free exchanges if you get the wrong size. It’s crazy how many Chelseas aren’t sold in half sizes.

3. The best boots are resoleable.

If you can resole them, they last longer. That makes them better value. The typical resoleable boot is made with a Goodyear welt, but this list includes several different construction types that vary in flexibility, waterproofness, and durability — but they can all be resoled!

4. Quality is relative to price.

Are there thousand-dollar Japanese horsehide Chelseas that are “better” than some of my favorites? Maybe. The average person would probably find them too stiff, heavy, expensive, and hard to order. But there are “boot guys” who would swear they’re the best.

The point here is that while exclusive leathers and arcane construction is cool, I’m writing for the average person who would Google “best chelsea boots,” here. The average person wants something that looks good, fits well, handles water, will last a long time, suits their use case, and won’t cost them an arm and a leg.

The boots on my list fit all those criteria. Well, except for a couple of the under $200 ones, which aren’t resoleable but still good value. I organized these picks in order of price so you can go by what you’re willing to spend. Most guys will stop at the first entry, and there are a lot of good reasons to!

Best Value Chelsea: Thursday Boot Company Cavalier

• Amazing value
• Wide variety of casual or dressy leathers
• Versatile look
• Unusually lightweight and comfy for a resoleable boot
• Wide fits, lots of sizes, and free exchanges
• $190

The best value Chlease boot is the Cavalier from Thursday Boot Company.

Thursday has four Chelsea models on offer: the outdoorsy Legend, the premium Journeyman, the casual Duke, and the Cavalier was meant to be the dressy one. But once they started offering it in casual leathers, it quickly became an all-round, all-purpose bestseller. (The “Sandstone” suede I’ve got is the most popular and the one they put in all their ads.)

Some dislike the lack of pull tabs, but personally, I prefer it this way because pull tabs always stick out from under your jeans.

They’re really lightweight — they’re the lightest on this list — yet they’re made with a hardy Goodyear welt construction that makes them resoleable and water resistant, and the comfort is further boosted by a layer of shock-absorbing foam on the insole.

Doing all this for under $200 is definitely remarkable. And so is the free sizing exchanges.

What I Like:

• The value. At $190 for Goodyear welted boots, these blow the competition out of the water.
• The versatility. The design can be easily dressed up or dressed down for everyday wear. (But grab a smooth leather if you want to go business casual.)
• The comfort. The shock-absorbing insoles add modern comfort to traditional construction.
• The range of leathers. These come in smooth, suede, and waterproof suede to suit any needs.
• The sizes. They have half sizes, multiple widths, and free exchanges on offer.

Downsides but not deal breakers:

• The leather sole has a layer of rubber underneath it, so you’re not getting the breathability of a straight leather sole.
• No pull tabs. I prefer this, but you might not.
• Lightweight. Again, they’re well made and real comfy, but it might not be the hefty boot feeling you crave. (But honestly, Chelseas usually aren’t.)
• Not every leather gets a wide-width option. It’s just three of them or so.

Best Budget Work Chelsea: Redback Easy Escape

• Lightweight with excellent shock absorption
• No break in experienced
• Durable, well-oiled leather
• Great for flat feet
• Available in soft-toe, steel-toe, or rubber-capped steel-toe versions
• Slip resistant and EH rated to 1,500 volts
• $153 – $215

“Wait, aren’t you a blogger or something? How did you properly test work boots?” I hired a water plant operator in Ohio, that’s how. One of our multiple work boot reviewers, Jeff Harmon, wore them to work for a month and found the Redback Easy Escape to be the best work Chelsea he’d tried.

The Redback Easy Escape isn’t resoleable, but the direct attach construction is more longlasting than most basic boots. Plus, Jeff interviewed two Emergency Medical Services employees who only wore this boot and had only needed two pairs in twelve years. Given it’s well under $200, that’s pretty good value.

This leather is oil-tanned for extra water resistance, and it’s very hard-wearing. The sole is also abrasion, oil, acid, and heat-resistant. The polyurethane midsole is great for shock absorption, and both that and the direct attach construction make it lightweight and flexible as well.

It’s a great all-round light duty boot that Jeff recommends for food service workers, mechanics, welders, carpenters, and factories. But if you’re wondering why we’d recommend a work boot with no steel toe, you actually can get the Easy Escape in a steel toe and an extra beefy version with a steel toe and an anti-scuff toe box cover. It’s a work boot that works with you.

What I like:

• The comfort. Lightweight, comfortable, and not hard to wear casually either.
• The value. Sometimes $155 on Amazon for the basic and $195 for the steel toe version is a great value.
• Made in Australia. If you don’t trust inexpensive boots made in the developing world, rest assured, Australia is a Canada-level developed country.
• Available in three versions. Soft and safety toes to suit how hard you need to wear them.
• The safety. EH rated for electric shock and very slip resistant.

Downsides but not deal breakers

• Hydrolysis: A downside with the polyurethane is that if you don’t wear regularly, the midsole can deteriorate.
• Not resoleable. But the price is fair and they last for years.
• Not ASTM rated for slip resistance, though they perform terrifically.

Best Waterproof Chelsea Boots: Ariat’s Wexford

• Waterproof, but still stylish
• A lightweight shank, helps with stability
• $200

This is the very, very rare example of a boot that’s waterproof yet still looks stylish. I know that “stylish” isn’t usually a priority for guys looking for waterproof boots, particularly if you’re shopping with the famously outdoor brand Ariat — but hey, it doesn’t hurt.

Because it’s not welted or resoleable, it’s very affordable: just under $200. Yes, Thursday’s Cavalier is cheaper than that, but the Wexford is still a very well priced boot.

What I Like

• The comfort. It’s got good stability from the shank and it’s pretty light and flexible because it’s not resoleable.
• The style. It’s not bulky or overbuilt like a lot of waterproof boots. This can work under jeans out on the town.
• The materials. Six leathers are available, including waterproof suede.
• The value. These cost under $200.
• The fit. They have a wide width available.

Downsides but not deal breakers:

• It can’t be resoled. But that’s practically always the case with waterproof boots.
• Modern construction won’t mold to the shape of your foot the way traditional boots do — in other words, there’s no leather underfoot that conforms to you with wear, which boot lovers will miss.

Best Whole Cut: Meermin’s Whole Cut Chelsea

• Made with just one piece of leather for a cleaner look
• Unusually lightweight for Goodyear welted boots
• Available in three lasts to suit different feet
• $240-$260

For a step up in fanciness, a lot of people like whole cut Chelseas: where it’s one piece of leather wrapping around the boot and stitched at the heel, so there’s no stitching under the elastic bit. The main benefit is that it’s a cleaner look, but some guys find it conforms better to the foot with wear.

Because they’re harder to make and it’s harder to get one big piece of usable leather, whole cut Chelseas are usually pretty expensive. But Meermin does whole cut Chelseas for a really good price, using really good leathers, for about $250 on average.

Another commendable thing is Meermin sells these on three different lasts, which basically means three kinds of fits, so you’re more likely to find one that works for you. I couldn’t wear Meermin until they released this one in their wider Negon last. Now I can! Hooray!

Just note they use UK sizing, which is about one size down from US sizes, so sizing can be tricky. For what it’s worth, I’m a 10.5 in my Meermin Chelsea, an 11 in Thursday, and an 11.5 or 12 in sneakers.

What I like:

• The comfort. Whole cuts might be more comfy, but the range of lasts to choose from gives them the real edge in the comfort game.
• The design. Whole cut looks cleaner, what can I say.
• The construction. Very classy whole cut construction at a great price.
• The materials. Meermin stands out for offering leathers from name brand tanneries, like Annonay calfskin and CF Stead suede, at this price.
• The price. They’re only $250.

Downsides but not deal breakers:

• The fit. Not great for guys with wide feet; there’s just one width available here, but a sized up Negon might be what you need.
• The sizing. UK sizing is hard to work out.

Best Casual Chelsea: Astorflex Bitflex

• Breathable and lightweight.
• Extra soft crepe rubber soles.
• Unusually roomy for a Chelsea
• Unusually cheap for Italian made
• $250

Astorflex’s Bitflex gets a lot of points for being unusually roomy, soft, and inexpensive for a resoleable boot made in Italy. These are such a good deal that discerning places like Leffot in New York City stock them, even though everything else they sell is over twice the price.

If you prioritize a soft sole, uncramped toes, and a particularly casual vibe, this family owned workshop outside of Milan has offered a solid option. But not too solid: the uncommon technique called ideal (sort of a cousin of stitchdown construction) makes them pretty light and flexible for what you’re getting.

This is a great option if you prefer to splay your toes. Chelsea boots tend to have a narrow toe box, but the Bitflex has a lot of room in the forefoot.

What I Like:

• The comfort.  I love that roomy toe and light weight.
• The materials. The crepe sole and suede upper contribute to the comfort.
• The casual look. If you worry that most Chelseas are too dressy, this is the option for you.
• The price. Italian made, resoleable, and $215? It doesn’t make sense. But I’m not complaining.

Downsides but not deal breakers:

• Not very versatile. The wide toebox is a boon for a lot of guys who like casual boots, but you might prefer a traditionally sleek look.
• The durability. The sole is soft, but the crepe rubber sole wears down pretty quickly.
• The construciton. No shank, this means they might not be ideal for long, long days on your feet. At least, not if you’re susceptible to foot pain.

Best Made-in-USA Chelsea: Red Wing Weekender

• Lightweight and flexible
• Tough work boot leather that ages well
• Made in Minnesota by the biggest name in American heritage boots
• $259.99

If you value American made or you like the classically tough Red Wing Heritage brand, I think their Weekender Chelsea is their most underrated boot.

Red Wing’s boots are often a hundred bucks more expensive than this and they’re quite stiff and heavy — which makes sense, since they’re modeled after classic work boots.

But while they have the chunkier Classic Chelsea for more of a work boot vibe, I think everyone’s sleeping on their Weekender.

Unlike almost every other Red Wing boot, it’s got an extra thin and soft crepe sole, an extra lightweight kind of stitchdown construction, and it’s lower profile than their work boots but the same tough leather. It’s just stupid easy to wear.

The underbuilt sole means you can feel bumpy terrain underfoot and the arch support is so so, but they bill it as a leisure boot and it fits the bill. Again, just super easy to wear.

What I like:

• The construction. Resoleable but lightweight and soft, a rare combination — especially from Red Wing.
• The leather. Uncommonly breezy construction with uncommonly tough leather is a cool combo.
• The comfort. Good shock absorption and no real break in.
• The value. $250 for an American made, resoleable boot is fantastic value.

Downsides but not deal breakers:

• The constuction. Made from several pieces of leather, so there are more seams than some folks like.
• The resoleability. It’s a bit harder to find someone to resole this boot than the more common Goodyear welt. It can be done, though.
• No shank, so-so arch support, and overall less sturdy than the heritage work boots you might be used to from Red Wing.

Best Smart Casual Chelsea: Grant Stone Chelsea Boots

• Excellent smart-casual Chelsea boots
• Famously consistent stitching and quality control
• Great value for this level of quality
• Some of the best leathers on the planet
• Made in China
• ~$400

Join me as we leave “great value” territory and venture into “boot guy” territory, where the hobbyists and aficionados are found and low prices are not so much of a factor.

For guys like that, this boot is considered great value at around $400, depending on the leather.

Chelseas tend to be pretty slim or pretty casual. It’s uncommon to get one that I’d call smart casual. Grant Stone is the undisputed king of the smart casual space in footwear, and I had to mention their Chelsea boot. I used to think of it as kind of stumpy, but I’ve grown to love it as offering something relatively fresh to the space.

Grant Stone is hugely popular among guys who want a high quality alternative to, say, $600 Chelseas. It’s true they’re not whole cut, but this brand is famous for fantastic quality control and for using leathers from the world’s most beloved tanneries.

The price is low because Grant Stone makes their boots in China, but at a world-class level. And they also stand out for having really good customer service: they’ll talk anyone through their sizing over Instagram or e-mail, they offer lightning fast size exchanges from their US distribution center, and they do plenty of sizes and wide widths.

What I like:

• The value. Incredible price for this level of boot.
• The construction. A surprisingly heavy-duty boot that’s made with a very high attention to detail and very high-quality construction.
• The materials. Grant Stone uses world-renowned leathers and has expert clicking.
• The comfort. If you like that sturdy, old fashioned boot feeling, this will satisfy you more than most others on this list.
• The fit. EE widths available and they’re great at helping you figure out your size.

Downsides but not deal breakers:

• The style. Not firmly dressy or casual.
• The constuction. Like I said, it’s got a more old fashioned boot feel than most Chelseas; you might not love that super stable feeling.
• They’re made in China. Some people don’t love that.

Best Rugged Chelsea: Bordon Isidro

• Handsome and versatile, but built like a Pacific Northwest work boot
• Double-row stitch down construction
• Vegetable-tanned leather uppers from Wickett and Craig
• Rabbit fur lining available for winter wear
• Excellent value
• $409 – $420

You probably won’t get these boots because they take six to nine month to arrive right now. But Stridewise’s editor Karl has a pair of these and when I was handling them the other day, I thought: this is the best “tough” Chelsea I’ve seen.

For various reasons, Chelsea boots aren’t that common for harder use, and sometimes when a brand does try to make a real tough Chelsea they just look weird.

But Bordon’s Chelsea looks great, can be worn anywhere, and yet it’s made ultra tough like a Pacific Northwest boot. I said the same thing when I reviewed their service boot.

Bordon is known for its versatile lasts and unusually tough builds. Double-row stitch-down construction is more common on logging boots, and they’re best known for the famously tough vegetable tanned leather uppers from Pennsylvania’s Wickett and Craig — the only kind of leather only the most discerning, hardest wearing boot guys want.

And you can even get them lined with rabbit fur if you want to wear them in sub zero!

At about $420-ish, it’s a very good price, but you’ll be waiting til next boot season to get them.

What I like:

• The materials. Really tough and rewarding leather that’s vegetable tanned the way we’ve been making leather for thousands of years. It’s rare.
• The fit. Excellent fit with a roomy but not too bulbous toe box.
• The construction: They combine a classic Chelsea look with an extremely tough build.
• The value: Fantastic value for the amount of labor and materials you get.

Downsides but not deal breakers

• The wait. They can take up to six months to arrive.
• The break-in. Difficult break-in: hey, you wanted boots built like logging boots.

Best Dressy Chelsea: Carmina Shoemaker’s Simpson

• Delicately lasted dress boots
• Uses box calf, a premium dress shoe leather
• Leather insole, midsole, and outsole for great comfort
• 10+ lasts to choose from to optimize fit
• $595

If you know dress boots, you know this is an uncontroversial pick for the best Chelsea to wear with a suit.

Carmina Shoemaker reside on the Spanish island of Mallorca, which I visited some time ago — but after I was already calling them the best dress boot!

One of the many cool things about Carmina is that they have dozens of lasts for every foot type and use case, including over 10 for their Chelsea boots. The Simpson last is their best-known, and I wear it with a suit all the time.

Calfskin is the default choice for dressy footwear and it’s Carmina’s specialty, offering a huge range of them from name brand tanneries. You even get the option of building totally customizable Chelseas if you prefer.

They’re really comfortable in a way you don’t often see in the US because they’re all leather underfoot: insole, midsole, outsole. Americans tend to shy away from that, but it gives a great balance of softness, durability, and ground feel, plus it’s very good at conforming to your foot’s shape with wear.

If you want to make absolutely sure you’ve got the perfect Chelsea to dress up as far as you want, this is the crème de la crème of luxury boots.

What I Like

• The materials. Glossy box calf leather from Germany has great shine and tight grain, earning its rep as one of the best leathers for dress boots.
• The fit. They have a wide variety of lasts, over 10 to choose from for these boots.
• The comfort. Three layers of leather in the sole make for a supremely comfortable, luxurious feeling.
• The construction. An unusually slim Goodyear welt construction. Usually, this construction is hard to dress up because it adds bulk, but you can see how sleek the boot is.
• The craft. I’ve visited the factory, and it’s great to know that they’re not only made in a developed country but also in one that’s gorgeous and spacious, with true artisans perfecting their craft.

Downsides but not deal breakers

• They’re hard to dress down. I mean, if you get a pair in suede then they’d look good smart casual, but then you can’t dress them up. You get it.
• Leather soles don’t have the best grip. I love them, but they’re not ideal on ice. Look, it’s a dress boot, you get it.
• They’re not cheap. A zillion years of history and craftsmanship in Western Europe mean these will run a good $600, but that’s less than half the price of industry go-tos like Yves Saint-Laurent.

Most Premium: Briselblack Bootmaker’s The Seventh

• Completely customizable from sole to lining
• Made with the finest leathers on Earth — or local leathers if you want to save cash
• Extremely rare and laborious old world construction methods
• Expect months for them to arrive
• ~$700

These last Chelseas are the most impractical on this list: expensive, hard to order, and take months to arrive. But you can’t talk about the best Chelseas without mentioning Briselblack Bootmaker.

On the Indonesian island of West Java, there is a 500-year-old city called Bandung where, due to a unique combination of Dutch colonialism, Chinese trade, and regional emphasis on craftwork, there is a thriving community of some of the world’s finest bootmakers.

And a small workshop of a half dozen rogues has made the curious name Briselblack world famous for making the most premium and exclusive Chelsea boots.

Every brand on this list welts and lasts their boots using machines. (Except Bordon, who hand last and do stitchdown, but still.) The guys at Briselblack Bootmaker hand last and hand welt these, which is much more skillful, laborious, and time-consuming.

But they have a waiting list months long because boot fans around the world consider this level of craftsmanship to produce better fits, better durability, and… well, a stronger metaphysical bond between craftsman, boot, and customer. It’s OK to say it out loud.

Now, will the average dude notice the difference between hand lasted and machine lasted? No. But this is a brand for the premium, high end, very discerning enthusiast — and guys like that drool at the thought of owning a pair of these Chelseas. I’ve owned two pairs.

What I Like

• Complete customizability: They’ll find you the leather you want, give you any combination of sole, stitching, and lining, etc.
• More handmade than almost any other boot: they take days longer to make than most of the other boots here.
• All the sizes: You’ll be asked to take measurements of your feet and they’ll adjust the last to accommodate you. I didn’t know my left foot was a quarter size bigger than my right until they told me — and I got the best fitting boots ever.
• The value. If you know what you’re getting, you know it’s an excellent price. They’d cost four figures if they were made in America.

Downsides but not deal breakers

• The order time, by a mile, is the worst thing. Depending on when you order, you’ll wait at least three months, maybe six.
• The price. Look, most guys won’t care to pay for all these extra handmade touches, and you also don’t get the option of a machine-made boot that would be cheaper than anything else here if it were made in Indonesia.
• The ordering process. It happens over Whatsapp, and that stresses out some guys. This brand is trustworthy, but I know it’s still nervewracking.

Wrapping Up

I own enough boots to sink a ship and am delighted to help you find the perfect Chelsea boot for your needs. Like I said way back at the start of this article, I’ve visited workshops and factories big and small all over the world to get a better grasp of how to understand and write about boots.

However, I didn’t come to these conclusions on my own — I’d like to thank the tens of thousands of YouTube subscribers who have shared their positive and negative experiences with these and other brands too, which helped me broaden and relativize my perspective. (You should subscribe. It’s a great crowd.) 

On a final note, Chelsea boots are unfairly pigeonholed as a dressy-but-not-that-dressy kind of shoe, but this list proves that the world of Chelseas is as vast as any other kind of shoe. — and I know there’s a style here for you.

Why Trust My Opinion?

Experience. An absurd, impractical, completely unique amount of experience. (You can learn more about our boot review process here.)

Heck, I’ve even made a pair of boots myself from scratch on a whirlwind trip to Guatemala, so I think I’m pretty qualified to list the best Chelsea boots for men.

Are Chelsea boots out of style?

No! The beauty of Chelseas is that they come in a variety of styles. Most are slim and ideal for casual or smart casual use, but they can dress up with a formal leather like box calf or dress down if they've got casual leather like suede or Chromexcel.

What kind of jeans do you wear with Chelsea boots?

Most Chelseas are quite slim, so they match best with jeans or trousers that taper from the knee to the ankle. The idea is that you don't want the disconnect of a loose, billowing cuff and a slim Chelsea peeking out from underneath. But if you're wearing more bulbous Chelseas like Blundstones, a looser jean is acceptable.

How formal are Chelsea boots?

Most Chelseas fit in the smart casual category: great with jeans, but slimmer jeans rather than baggy ones. So long as your outfit is fitted, any Chelsea will work well. That said, some brands (like Carmina) make dress Chelsea boots that can be worn with a suit. Look for smooth, glossy leathers and leather soles for dressy Chelseas.

Are Chelsea boots supposed to be loose at the top?

Because they aren't laced up, Chelseas are often a little loose at the ankle, but what matters is your heel: if it isn't slipping, the fit is fine. If it is, buy a tongue pad to fill the space in the instep at the top of the foot. Surprisingly, this is the best way to stop heel slippage.

Are Chelsea boots good for walking?

They were originally invented as walking boots! Chelseas are great for spending all day on your feet, but if you're prone to foot pain, look for one with a heel and a shank, since they'll improve stability.