13 Best Chelsea Boots for Men Tested | Comfortable, Work, Budget, and More

After nearly five years of reviewing boots, I’ve finally landed on my list of the best Chelsea boots for men. Need something sleek you can wear with a suit? I got you. Something steel-toed and heat-resistant? Right here. Are you just a normal dude who wants a pair of boots that look good and will last a long time? That’s first on the list.

Our Top-Picks

• The Best Men’s Chelsea Boot: Koio’s Trento
• Most Customizable Chelsea: Idrese Shadbolt
• Best Value Chelsea Boots: Thursday Boot Company Cavalier
• Best Waterproof Chelsea Boots: Ariat’s Wexford
• Best Luxury Chelsea Boots: Briselblack’s Seventh
• The Most Comfortable Chelsea Boots: Astorflex’s Bitflex
• Best Dress Chelsea Boots: Carmina
• Best Luxury Runner Up: RM Williams Comfort Craftsman
• Best Work Chelsea Boots: Blundstone 990
• Cheapest: New Republic’s Sonoma
• Most Versatile: Parkhurst’s Elmwood
• Best for Wide Feet: Adelante’s Mendoza
• Best Chunky Chelsea: Red Wing’s Classic Chelsea

Meet Our Expert

As mentioned above, I’m a professional boot reviewer. (I know, it’s a weird career choice.) I’ve been making YouTube videos since early 2018 and publishing articles for just as long about everything you could possibly want to learn about boots, from the importance of a shank to the best creams for conditioning leather footwear.

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.

[Related: My list of The Best Boots for Men]

1. The Best Chelsea Boot Overall: Koio’s Trento

Koio makes the best leather Chelsea boots of all time: The Trento. They started as a sneaker brand, but after rising to the top of that market, they branched out into making boots for men.

There are three leathers available. The brown suede is the most versatile. The black leather one is a great dress boot. The “Cardamom” (cream) one is very classy.

Made in Italy with Italian components, the Trento is sleek, handsome, fully leather lined for comfort, and has a hard wearing Blake stitch construction that keeps it water resistant and resoleable. 

What I Like About Koio’s Trento

• The Blake stitch construction. This keeps the boot lighter, slimmer, and more flexible than the common Goodyear welt, so it’s much more long lasting than cemented boots.
• The leather sole. A criminally underrated sole, leather breathes well, conforms to your foot with time, and adds to the boot’s light weight and flexibility.
• The sustainability. Koio only uses leathers certified by the Leather Working Group. They ensure that no toxic runoff is produced during the tanning process.
• The comfort. The leather midsole and outsole conform nicely to the foot with wear, and a shock absorbing insole helps with… absorbing shock.

What I Don’t Like Koio’s Trento

• No half sizes or wide widths. You’re meant to size down if you’re between sizes, but I found the boot fits very well.  
• The suede is untreated. If you’re worried about staining cream suede (and why wouldn’t you be?) you need to pick up their suede protector.
• It’s not ideal for stormy weather. Light showers are fine, but don’t go splashin’.

[Related: My list of The Best Leather Briefcases for Men]

2. Most Customizable: Idrese Shadbolt

There are three really cool things about Idrese’s Chelsea boots.

The first is that the leather is hard-wearing, roughout leather. It’s super durable and looks better the more you beat it up.

The second is that it’s very water resistant because it’s made with a reverse storm welt that keeps water getting where the boot is stitched together.

Third, you can design your pair yourself. Their site has an unreal feature that enables you to make a boot with any kind of leather, sole, and construction method you like — you can even put panels of wool or flannel on there if that’s what you’re feeling. 

What I Like About the Idrese Shadbolt

• The Shadbolt is a great mixture of refined and hard wearing. The roughout leather upper, storm welt, and Ridgeway sole are all ways to make it able to weather any storm while staying low profile and sleek.
• You can design any heckin’ boot you want. Want some tartan flannel on there? Feel like a leather sole? Anything you’re feeling, you can design.
• They’re durable. These boots are completely resoleable.

What I Don’t Like About Idrese Shadbolt

• The shoes take a couple of months to be made. Them’s the breaks when you want freshly made boots.

3. Best Value Chelsea Boots: Thursday Boot Company Cavalier

The best value is Thursday Boot Company’s Cavalier. This classic Chelsea boot is Goodyear welted and has a phenomenally low price of $190. It’s also available in a huge variety of leathers, from dressy cowhides to waterproof suedes.

I picked up the Sandstone, a light snuff suede, and immediately wore it all over Europe for several months last year.

During my trip, I found myself reaching for this model over and over again, whether I was dressing down in a denim jacket or going smart casual in a button down and pea coat.

[Related: Looking for a versatile, casual shoe? Check out our list of the best loafers for men]

What I Like About Thursday Boot Company Cavalier

• The value. At $190 for resoleable boots, these blow the competition out of the water. Anyone else making a boot like this would charge a solid $100 more.
• The versatility. The design can be easily dressed up or dressed down. (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.

What I Don’t Like About Thursday Boot Company Cavalier

• 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. Actually, I hate the way pull tabs always wind up sticking out from under my jeans, so this is a “pro” for me, but a lot of guys prefer them.

4. Best Waterproof Chelsea Boots: Ariat’s Wexford

The best waterproof Chelsea is Ariat’s Wexford.

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 cheap: just under $200.

What I Like About Ariat’s Wexford

• It’s comfortable all day thanks to the lightweight shank, which helps with stability.
• It’s not bulky or overbuilt like a lot of waterproof boots are. This can work under jeans out on the town, no problem.
• Six leathers are available, including waterproof suede.
• The value, these cost under $200.

What I Don’t Like About Ariat’s Wexford

• It can’t be resoled, but that’s almost always the case with waterproof boots.
• Modern construction won’t mold to the shape of your foot the way traditional boots do.

5. Best Luxury: Briselblack’s Seventh

Briselblack is a tiny company in Bandung, Indonesia, which has become the global epicenter of fine footwear. Briselblack and Chelsea boots have become synonymous, and many qualified folks call their hand-welted Seventh boot the best Chelsea boot on Earth.

You can only order over their WhatsApp or Instagram. Also, when you get imported leather (mine is waxed horsebutt from Italy’s Maryam tannery). They cost about $500 and will take at least three months to arrive.

What I Like About Briselblack’s Seventh

• It’s one piece of leather, which is very rare and means they conform to the foot better than anything else.
• They’re handwelted, which requires hours of skilled labor versus the seconds it takes to Goodyear welted boot. Many find it more comfortable because of the thicker leather required.
• The top-notch components. My leather is a vegetable-tanned horse from a world-famous Italian tannery, and you can get any leather you want.
• They’re customizable. Anything from the sole to the leather to the color of the stitching or the welt.

What I Don’t Like Briselblack’s Seventh

• The order time, by a mile, is the worst thing. Depending on when you order, you could be waiting over six months.
• The price, even for Indonesian boots, is high — mine cost $500, and with Indonesian leather, they’d be over $400. Still, if they were made stateside, they’d be $ 1,000, easy.

6. The Most Comfortable Chelsea Boots: Astorflex’s Bitflex

After Thursday, the runner-up for best value Chelsea boot is Astorflex’s Bitflex. Other than the fantastic value, another cool thing is that they have a soft, flexible, comfortable crepe rubber sole.

This is a great option if you have wider feet. Chelseas tend to have a narrow toe box, but the Bitflex has a lot of room in the forefoot. It looks more casual, but it’s very comfortable. It’s even friendly on E-width feet.

It’s crazy value and super comfortable. 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.

What I Like About Astorflex’s Bitflex

• The comfort. The combination of crepe sole and suede upper makes for breathable, lightweight, and flexible boots.
• The width. A lot of guys with wide feet have trouble buying Chelseas. These are roomy enough at the toe to accommodate wider guys.
• The price. Italian made, resoleable, and $215? It doesn’t make sense. But I’m not complaining.

What I Don’t Like About Astorflex’s Bitflex

• 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.
• 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.

7. Best Dress Chelsea Boots: Carmina

If you want a luxury Chelsea boot that looks good with a tailored suit, these are it.

They have a slightly pointed toe and elongated forepart. Their Simpson last is elegant and will silence any concerns about dressing up boots.

If you want to make absolutely sure you’ve got the dressiest, sleekest, most delicately lasted Chelseas around, this is the crème de la crème of luxury boots.

What I Like About Carmina’s Chelseas

• 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 variety of lasts. With over 30 to choose from, any kind of foot or intent can be accommodated here.
• Three layers of leather in the sole make for a supremely comfortable, luxurious feeling.
• An unusually slim Goodyear welt. Usually, this construction is hard to dress up because it adds bulk, but you can see how sleek the boot is.
• I’ve visited the factory and it’s great to know that they’re not only made in a developed country, but one that’s gorgeous and spacious with true artisans perfecting their craft. (Seriously, check the video.)

What I Don’t Like About Carmina’s Chelseas

• They’re not that versatile. This shouldn’t be a surprise: they’re formal boots, not for t-shirts!
• Leather soles don’t have the best grip. I love them, but they’re not for icy weather.
• They’re not cheap. A zillion years of history and craftsmanship in Western Europe mean these will run a good $570, but that’s less than half the price of industry go-tos like Yves Saint-Laurent.

Other examples: Carmina, Thursday’s Cavalier, Koio’s Trento, Ace Marks

8. Best Luxury Runner Up: RM Williams Comfort Craftsman

The runner-up for the best luxury Chelsea is actually more expensive than Benzein’s because they’re made in Australia. Still, they’re much easier to buy, and their reputation is sterling. If they weren’t so expensive, I’d make these the top pick.

What I Like About RM Williams Comfort Craftsman

• The wholecut leather means it’s extraordinarily comfortable from day only gets better.
• The Yearling leather is a rare combination of soft and hard-wearing.
• They’re quite versatile and easily dressed up or down.

What I Don’t Like About RM Williams Comfort Craftsman

• They’re pretty expensive, ranging from $539 to $590.
• Everyone doesn’t love the slightly square toe.

9. Best Work Chelsea Boots: Blundstone 990

The for work is Blundstone. This Australian brand is world famous for their casual Chelseas. They’re inexpensive, and they look pretty good as streetwear. They don’t have waterproof leather, but they are water resistant, so they’re decent for cold winter weather.

This one levels up by being heat resistant to 572 degrees Fahrenheit, it’s electrical hazard resistant, oil and acid resistant, slip resistant, and water resistant, and it has a steel toe.

It’s not resoleable, but the average work boot isn’t. Plus, the fact that it’s not welted keeps the price relatively low at just $230.

What I Like About the Blundstone 990

• They’re resistant to almost everything: heat, electricity, water, oil, and acid.
• The steel toe will protect your toes on a job site.
• There’s a steel shank, unusual for a boot like this, and it’ll help provide stability and prevent sore feet when you’re standing all day.
• The removable footbed offers arch support but gives you the option of using orthotics instead if you need to. 

What I Don’t Like About the Blundstone 990

• They can’t be resoled, which is unsurprising for this kind of boot.
• Difficult to get a perfect fit for some guys, try them on first, when possible.
• They’re made in Asia, but they have “Australia” all over the branding and the pull tabs. Deceptive!

10. Cheapest Chelsea Boots: New Republic’s Sonoma

Note that the cheapest is not the same as the best value because I think the best value will last longer than one sole. For men, the best boots are repairable and resoleable. You can wear them much longer and get that cool beat-up look.

If you’re looking for a nice boot that’s under $100, check out the very famous Sonoma boot from New Republic for about $85 or $90.

These Chelsea boots are famous for their super soft and comfy crepe sole and light, flexible construction. They basically cost as much as a pair of sneakers and will last much longer than Chuck Taylors.

What I Like About New Republic’s Sonoma

• The price tag. These cost as much as a pair of sneakers, and pretty inexpensive sneakers at that.
• The soft crepe sole. 
• The lighter weight and flexibility of cemented construction.

What I Don’t Like About New Republic’s Sonoma

• They can’t be resoled when the crepe wears through — and crepe isn’t the most durable sole.
• It’s not the most stable shoe because of the construction, sole material, and lack of a shank.
• They’re made in China. I actually don’t care about this, but you might.

 11. Most Versatile: Parkhurst’s Elmwood

Parkhurst is a very small brand with a very dedicated following among boot hobbyists. It’s more water-resistant than your typical welted boot but works well in smart casual situations. It’s not super rugged like a hiking boot.

Just be sure to pay attention to their sizing section; I wound up needing to order a half size smaller than my usual boot size.

What I Like About Parkhurst’s Elmwood

• The versatility, with a classic silhouette. 
• The water resistance. Not only are these made with a storm welt, but the elastic goring is a Gore-Tex weave that’s great in wet weather and won’t stretch out too fast.
• The fit. Parkhurst weaves a kind of magic that makes the boots look sleek while actually offering a lot of room in the forefoot.
• The owner, Andrew. He’s a cool dude. Check out this interview we did.

What I Don’t Like About Parkhurst’s Elmwood

• The availability. Parkhurst often has difficulties keeping products in stock.

12. Best for Wide Feet: Adelante’s Mendoza

This one’s a no-brainer. Adlente owns and runs their small workshop in Pastores, Guatemala, that’ll build and send your boots in under two weeks. On top of that, they treat employees really well.  Adelante’s craftspeople earn twice the local wage and enjoy a range of other benefits you can learn about in the video below.

But the headline is that they offer a huge range of sizes and widths: up to size 17 and up to EEEEE width.

What I Like About Adelante’s Mendoza

• The availability of sizes and widths. I’m a pretty normal 11D myself, but Adelante’s model lets them sell up to 17EEEEE. I’ve received multiple tearful letters from wide-footed men who had never before been able to wear good boots.
• The speed. Made-to-order in just a couple of weeks is unheard of. Usually, you’ve got months to wait.
• The sustainability. Adelante was founded by two Americans who wanted to bring more stability and prosperity to the shoemaking industry in Pastores, and they rigorously track their results. 
• The price. $305 for made-to-order welted boots in impossible sizes? Get outta here.

What I Don’t Like About Adelante’s Mendoza

• Some find the outsole could be grippier.
• Not everyone wants to wait for their boots. During the holiday season, I’ve seen wait times up to six weeks.

13. Best Chunky Chelseas: Red Wing’s Classic Chelsea

The last entry on our list is the chunky Chelsea from Red Wing, for guys who want a pull-on boot that’s also roomy.

Red Wing Heritage makes boots the old-fashioned way: robust American leathers, thick leather midsoles, cork filling — footwear that’ll last a million years and look cooler as they age. (Just like you will, right!?)

What I Like About Red Wing’s Classic

• They’re comfy! Red Wing Heritage makes boots the old-fashioned way, but the Classic has a softer insole that limits break-in and helps shock absorption.
• They breathe well thanks to an unusual mesh on the toebox’s interior that circulates air.
• Red Wing makes their classic leathers in their tannery in Minnesota, and they’re famously hard-wearing and beautiful. The patina will be fire.
• The roomy fit make for a rare silhouette that was definitely needed in the market as an alternative to all the slim Chelseas.

What I Don’t Like About Red Wing’s Classic

• The things that make them comfy? By that I mean a lot of people were upset that old fashioned bootmaker Red Wing tried out newfangled foam and mesh in the Classic Chelsea. And, I think it’s fine, but you know how purists are.
• The way the leather’s stitched together, with that one big panel for the forefoot and various seams between there and the heel… it’s not the most aesthetically pleasing look to some guys.

Wrapping Up

I own enough boots to sink a ship and am delighted to help you find the perfect Chelsea boot for your needs. However, I didn’t come to these conclusions on my own. So, I’d like to thank the tens of thousands of YouTube subscribers who have routinely shared their positive and negative experiences with brands and models. (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 shows that there’s a style out there for you.

Are Chelsea boots out of style?

No. The beauty of Chelseas is that they come in a variety of styles. The slimmer versions are ideal for tapered jeans while bulkier versions like Blundstone or Red Wing are better suited for loose jeans and casual wear. Suede is the most versatile material if you want a Chelsea that can be worn with anything — just match the boot to your pants and you'll be set.

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 cuff 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 top. The most important element of the fit with this kind of boot is your heel: if your heel isn't slipping, you can be confident in the fit.

Are Chelsea boots good for walking?

They were originally invented as walking boots! Chelseas are great for spending all day on your feet, just make sure if your Chelsea has a heel that it's constructed with a shank, which improves stability and reduces foot pain with long walks.