10 Most Comfortable (kinds of) Boots

Ever since I started this blog about boots and started wearing every kind of boot from every kind of brand, people have been requesting a list of the most comfortable boots.

The problem is that different people find different things comfortable. Soft or stable? Groundfeel or grip?

But after many years of talking about boots, reviewing boots, traveling to boot factories, and even making my own boots, I think I can finally, authentically write this list.

I’m going to do that by first discussing six kinds of comfort, then I’m going to give you four ways some brands can make better fitting boots than you might have thought possible.

That’ll bring this list to a nice round 10 most comfortable boots — or more accurately, ten most comfortable kinds of boots — with product recommendations for each.

How We Picked the Most Comfortable Boots

Man, I’m glad you asked, because I put a ton of work into this list.

In fact, I put seven years into it: that’s how long I’ve been personally covering boots on this website and on my YouTube channel, where I’ve posted hundreds of reviews and guides.

Not satisfied with being just some guy who wears lots of boots, I’ve also spent these years getting as much education from the experts as I can: I’ve visited factories and workshops in over a dozen countries from India to Spain, and I even made my own boots in Guatemala with leather I made myself in Mexico.

I also enlisted the help of four other boot YouTubers to round out this article, which will include pointers from Rose Anvil, Carl Murawski, Bootlosophy, and YouShoe.

One final point: we’re mostly talking about boots to wear casually, not professionally. Whether you’re blue or white collar (they’re both in that ‘professional’ category), most guys need a boot to wear off the clock that can manage rain, look cool, and save you money by lasting way longer than sneakers. That’s the kind of boot I’m emphasizing here.

1. Boots With No Break In

• Means: Better shock absorption, lighter weight, more flexibility, and easier break-in
• Uses EVA or Poron instead of stiff leather for instant softness
• This is a big factor in reducing break in, though you also need a leather upper that’s not too stiff either
• Brands: Thursday Boot Co, Helm, R.M. Williams

First, I’m going to talk about boots with soft insoles. Traditionally made, resoleable boots are typically made with a thick slab of vegetable tanned leather for the insole under your feet, and while there are plenty of benefits to that, it’s also the main element that clashes with modern approaches to comfort.

There are plenty of good reasons some companies swap the leather insole for sneaker-like foam like Poron or EVA, and I’m not just talking about the fact that these boots sell better for the brand.

Softer insoles mean better shock absorption, flexibility, lighter weight, and you might be surprised to learn that it improves the break in process too: the pain experienced from breaking in boots comes from not just the leather upper softening to your foot’s shape, but the leather insole doing so as well.

Best Boot Brands With No Break In

Thursday Boot Company: They became the most popular casual boot brand in the United States in large part because the foam insole and softer leathers fixed the break in problem that kept so many guys from trying boots.

These days they sell some boots without the foam, but most of their bestsellers like the Captain (my most worn) and Diplomat (Bootlosophy’s favorite) fit the bill. Just avoid the “Rugged and Resilient” leathers if you want to absolutely minimize the chances of a bad break in.

Helm: Extra light and flexible from not just the spongy insole but also because they’re made with the unusual Blake Rapid construction.

R.M. Williams: An example of a high end brand leaning into foamy insoles, see their Comfort Craftsman, and Turnout boots. Those are very high-end examples of resole boots that use soft foam underfoot.

Thorogood: Inexpensive, Goodyear welted work boots that are easy to wear casually and are made with soft insoles. Personally, I wouldn’t usually love a boot without any leather underfoot at all, but it certainly helps for this purpose.

Keen’s: Another work boot brand that YouTuber and leatherworker Rose Anvil told me are his favorite pick for comfort. “Semi traditionally without too much squish” is a good balance.

2. Boots With Soft Soles

• Means: Better shock absorption while retaining the “custom” feeling of leather insoles
• Look for soles described with the words wedge, Cristy, blown rubber, polyurethane, PU, and/or crepe
• Most commonly seen on desert boots and moc toes

Traditional boots are all about stability, not springiness, but this is a more traditional, less high-tech way of improving a boot’s underfoot softness than the last entry.

Because of their popularity on jobsites, moc toe boots are most often found with wedge soles — that’s the kind of spongy sole that’s flat so as to keep your heel from tripping on nails and the like. They’re sometimes called Cristy soles.

Crepe Soles

And then there are crepe soles, which are not always the same thing as a wedge sole. Made from the coagulated latex of the rubber tree, crepe soles are as old fashioned as soft soles get. It’s most common on what are probably the lightest, squishiest, and most breathable boot that can still be resoled, which is the desert boot.

Best Boots With Soft Outsoles

Most moc toes, including the famous Red Wing Classic Moc and the more luxurious Grant Stone Brass Boot.

For the extra light, flimsy, and breathable desert boot category, Clark’s Desert Boot is the most popular model, though it’s very hard to resole. (The price matches the quality, though.)

Higher quality desert boots that are resoleable but still hit the right notes are Astorflex and Red Wing’s Weekender Chukka.

(Obviously, if soft and light is your priority, you can always get cheap, non-resoleable boots like Cole Haan or Johnson and Murphy. But like, come on. I’m trying to get you into long-lasting stuff, here.)

3. Boots With a Roomy Toe Box

• Means: Your toes can splay and move naturally
• Dedicated work boots usually have a lot of volume for this reason
• Look for boots made on the Munson last, or something likened to it

A lot of guys looking for comfort will prioritize a roomy toe box. If you haven’t purposely looked for one, you might have stopped noticing that your pinky toe usually rests against the inside of your footwear and that your average almond-toed, smart casual boot is not the shape of a human foot.

But when you wear boots that allow your toes to splay out, it’s really, really nice — even though you are usually opening yourself up to people calling your boots “clown shoes” or “duck bills.”

Best Boots With Roomy Toes

Most work boots are roomy enough for dynamic movement, but this list (and website) emphasizes boots you can (also) wear after work, so..

Oak Street Bootmakers make my favorite in this category. Their Elston last is what they use on their World War-inspired service boots, the Trench and the Field boots, and it’s based off the Munson last. (The Munson was designed to fit as many soldiers’ foot types as possible.)

Other casual boots with big round toes are Red Wing Heritage‘s “Number 8” last they use on their famous Iron Rangers and Blacksmiths.

Chelsea Boots With Roomy Toes

Side note: it’s particularly hard to find Chelsea boots with roomy toes, so here I’ll mention that Red Wing make their Classic Chelsea (not the Weekender Chelsea) on the same Number 8 last as the Iron Ranger.

Astorflex’s Bitflex is another good option for a roomy toe, especially since it’s also got an aforementioned crepe sole and it has an unusually flexible kind of resoleable construction called ideal stitch.

Meermin’s Chelsea, specifically on the Negon last, is also worth a shoutout. The brand is Spanish and Europeans tend to prefer slimmer fitting footwear, so I was very happy when they finally released a Chelsea in this wider, more American-friendly fit.

Other roomy Chelseas would be the very popular ones from Blundstone, Dr. Martens, and Redback, but remember that these can’t be resoled.

4. Barefoot Boots

• Means: Wide toe and a very thin, very flat sole
• Ultra-lightweight with minimalist structure
• Brands: Origo, Jim Green, Lems, and Bearfoot

Since we’re talking about the fact that footwear is almost never shaped like a foot, let’s discuss barefoot boots.

They’re also made so that you can splay your toes as wide as you like, but they also have very thin soles and no heel. This is to get you as close to the ground and simulate the feeling of being “barefoot” as much as possible.

You might be confused as to why some boots are all about building up as much support as possible and some boots are about providing as little support as possible. I answered your questions in this pretty interesting interview with a podiatrist about when this kind of footwear might be useful.

Best Barefoot Boot Brands

Jim Green are probably the best brand for selling barefoot boots: they come in a range of styles including lace up, Chelsea, and moc toes.

Origo have fewer models, but they’re the only other brand I know of that gets relatively close to replicating the look of the other classic leather boots on this list.

Lems and Bearfoot are well known for their barefoot boots if you’re OK with models that are a bit more geared toward hiking and movement.

Duckfeet, lastly, is a Scandinavian brand that make wool-lined winter boots that are as close to barefoot as you can reasonably get for a winter boot. They’re resoleable and have natural crepe soles.

Two things to note: one is that with their much bigger emphasis on thin soles, barefoot boots usually can’t be resoled.

The other is that, with the exception of less-thin-soled brands like Duckfeet, you don’t want to wear barefoot boots when it’s really cold. The coldness of the ground travels straight into your feet — hey, you wanted to feel like you weren’t wearing shoes!

5. Boots with Leather Soles (and Insoles, and Midsoles)

• Means: All leather underfoot means your boot will better conform to your foot’s shape and it offers a balance of support, softness, and groundfeel that many adore
• Not grippy on carpet or tile, but totally fine everywhere else
• Brands: Wolverine, Grant Stone, Carmina Shoemaker

The next entry that many guys swear is all important for comfort in a boot is: boots with all leather underfoot. I’m talking leather insole, outsole, and a midsole if it’s got one.

If you’re a traditionalist, you’ve probably been horrified by all the talk of synthetics and softness in this list, perhaps even asking, “What’s the point of a boot if there’s no leather underfoot?!”

For those unaware: boots made like this conform to the shape of your foot over time, producing a completely distinct kind of comfort and support that you don’t get with rubber.

The fit and comfort of boots with leather insoles and rubber outsoles also improve with time, but the experience is different when it’s leather-leather-leather.

Compared to similarly made boots with grippier rubber soles, leather soled boots are more flexible, breathable, lightweight, they break in more easily, and they offer a lovely-if-impossible-to-describe sensation of groundfeel. Your feet are protected, but you get a much more tactile sensation of walking around the world.

Best Boots With Leather Soles

Wolverine’s 1000 Mile stands out for having a leather insole and outsole with no midsole, so it’s got more flexibility and groundfeel than others in this category.

Grant Stone makes a ton of smart casual boots, including their plain toe Diesel and the split toe Ottawas I bought my Dad, with a more sturdy build of thicker leather insoles, midsoles, and outsoles.

Carmina Shoemaker is a higher end Spanish brand that make a lot of boots with that same build but with thinner leathers, and they also offer options for customization.

6. Genuine Handsewn Moccasin Construction

• Means: One piece of leather cradles your foot and is stitched at the top, conforming to your foot’s shape unlike anything else
• Brands: Russell Moccasin, Rancourt & Co, Jim Green

This is the last kind of boot entry before I get into how brands offer better fitting boots.

It’s an extremely niche entry, but there is a type of moc toe boot called genuine hand-sewn moccasin construction that a lot of guys swear is the most comfortable footwear possible.

I visited a factory that makes them in Maine, Rancourt & Co, and long story short: they’re basically upside down boots. Instead of the leather coming over your foot and getting stitched to the sole, there’s one piece of leather that goes under your foot and then it gets stitched on top to the “plug.”

This means your foot is swaddled in a single piece of leather without seams or footbed, and it offers a form of comfort that’s unlike anything else. It’s also pretty waterproof for a traditionally made boot, plus getting one of these boots means you’re keeping a rare form of artisanal shoemaking alive.

Best Genuine Handsewn Moccasin Brands

Rancourt & Co, with their emphasis on the pliable and beautiful Chromexcel leather, might be the top pick for comfort.

Russell Moccasin in Wisconsin is the other famous American brand, and with their history in the world of hunting and their range of boots with multiple vamps, they’re your pick for more outdoorsy genuine moc toes — my Backcountry‘s are more waterproof than anything else on this list.

Jim Green in South Africa also make them. They’re a bit less handmade than the others on this list, but they’re also a lot cheaper and they arrive a lot faster; Russell and Rancourt usually need you to wait a few months to get your boots.

7. Boot Brands With Lots of Widths

• Means: Many don’t know if they have narrow or wide feet and most brands only offer one or two widths anyway — some offer several times as many widths to get a more ideal fit
• Brands: Nicks for casual, Alden for smart casual, Allen Edmonds for smart

Now, I’m going to talk about four increasingly advanced ways that some brands can give you a better-fitting boot than you might have thought possible.

The first is just widths. Most brands offer the standard width (a.k.a. a “D” width) will offer one wide size (if they offer one at all) and almost nobody offers narrow options, but getting the exact right width can make a pretty significant difference for your fit.

And I think most guys go their whole lives without knowing they have an unusual width: I was writing about boots for years before being told I probably had a “C” width foot, but nobody makes C-width boots.

Best Boot Brands for Wide Feet

Nicks Handmade Boots in the Pacific Northwest offer up to 9 widths on many of their super rugged boots, including narrow ones. You’ll need to wait a few months for them to get made for you, but they’ll probably be the last boots you’ll ever need.

Alden are an American institution who make Indiana Jones’s boots up in Massachusetts, and they offer them in six widths that include two narrow ones. You’ll probably need to wait for them to be made for you as well. And I’ve heard Alden can take up to a year.

Allen Edmonds should really top this category though: they’re made in the United States, they’re ready to wear (no waiting for them to be made), and some of their models (like our favorite dress boot) are sold in ten widths.

8. Boot Brands With a Wide Variety of Lasts

• Means: All footwear is made on a last, a foot shaped mold that dictates the final fit and shape. The more lasts a brand uses, the more likely you’ll find one that’s just right for your foot.
• Brands: Carmina Shoemaker, Meermin Mallorca, and Blkbrd Shoemaker.

Another way to find the most comfortable boot of your life is to find a brand selling boots made with lots of different lasts.

A last is the foot-shaped mold that dictates a boot’s fit, and you might have forgotten that a foot doesn’t look like a brick: it’s not just one width and one length. Every foot has particularities.

To find out what’s notable about your feet, I’d recommend going to a shoe store to get your foot measured and asking the clerk. Do I have a low instep, high arches, narrow heel? Get all the info you can and use it to find a last that works for you.

It’s a lot more common for a dress shoe brand to sell a lot of lasts than a boot brand, but you have options.

Boot Brands With Lots of Lasts

Carmina Shoemaker always come to mind here: European brands tend to like slimmer fits, which means they’ll often put more work into making more lasts to contour more types of feet: they sell over 30 different lasts.

Meermin Mallorca is a cheaper Spanish brand with twelve lasts. They’re not all for boots, but still, I was so happy when they finally released a wider fitting last, the Negon. (European boots tend to fit really tight for Americans.)

Blkbrd Shoemaker in India have about about nine lasts, and they made the cut here because they’re especially great at custom orders: if you like the sound of a last that they made for their dress shoes, they can make you something casual on it.

9. Boot Brands That Customize Lasts

• Means: You send your foot measurements and the maker will add material to their existing last to better fit you
• Brands: White’s, Limmer, Blkbrd, and Indonesian brands like Briselblack and Onderhoud

The second-to-last level of getting a perfect fitting boot is to find a brand that will customize their last for you.

That means you take measurements of your feet and, if they need to, they’ll add a bit of extra leather here and there on their last to make it closer to your foot.

I’m actually a quarter size bigger on my left foot and nobody makes quarter sizes — but Briselblack, a maker in Indonesia, customized their last for me.

Best Brands that Customize Lasts

Limmer boots: “My most comfortable boots at the moment are probably my custom Limmer boots,” says Boot YouTuber Carl Murawski. “They were made to my feet and have broken in perfectly. I’d think nothing of throwing them on for a long, long day on my feet.”

White’s in the Pacific Northwest told me that they’ll often perform this service for customers, and so will a lot of smaller Asian brands like (again) Blkbrd Shoemaker in India, and some Indonesian brands like Briselblack and Onderhoud.

10. Bespoke Lasts

• Means: A craftsperson makes a last from scratch to perfectly fit your feet — both of them.
• The most accurate, personalized fit possible in any footwear
• Extremely rare, expensive, and usually only done in person
• Brands: One-man shops like Francis Waplinger and Stefano Bemer in New York and White Kloud in Japan

And the final boss of comfort: finding a bootmaker who will make you a bespoke last.

This is not modifying an existing last with a bit of leather and nails. It’s making a whole new last based off of your foot.

It’s extremely rare, extremely expensive, extremely time consuming, and only done in person — but nothing can beat a boot made for your foot.

Best Bespoke Boot Brands

This is usually a service done by one-man workshops and only in person, so I’m unlikely to be able to do much more for you here than to tell you this service exists and to Google it in whatever areas you’re willing to travel to.

Here in New York I know Francis Waplinger and Stefano Bemer (who has more casual options), and probably the best known bespoke bootmaker is White Kloud in Japan. You have to fly there to be assessed by him, and maybe he’ll agree to let you pay him thousands of dollars for this service. If you’re really nice.

Honorable Mentions

I wanted to cap this list at ten entries, but here are some less popular options that some guys swear by.

Blake Stitched Boots

Resoleable, longlasting boots are usually stiff and heavy because they’re made with Goodyear welt construction.

Another way to make durable footwear is the less common Blake stitch. They’re a little less water resistant and it’s a little harder to find a cobbler who will resole them, but many consider that worth it for what you gain in lightness, flexibility, and groundfeel — they’re also a bit cheaper to make.

Best Blake Stitched Boots

Beckett Simonon is the king of the comfortable-but-not-fragile Blake stitched boot. They’re inexpensive and have a huge range on offer, but you need to wait a few months for them to be made for you.

Koio make some pretty great (if kind of pricy) Blake stitched boots too, while Taft has some good (if flamboyant) options with soft rubber soles.

Sprung Toe Boots

Sprung toe lasts look a little wild, but plenty of people enjoy the way that the boot’s shape facilitates a rolling motion when you walk by compensating for the natural angle of the foot. Others hate them because it holds the toes in an unnatural position.

But hey, Viberg wouldn’t be selling a whole range of thousand-dollar sprung toe boots if there weren’t a lot of guys who swear by them! (A slightly cheaper and less dramatic option is Truman Boot Co‘s work boot last.)

Non-Resoleable Boots

Finally, I emphasize resoleable boots on this site. But as you might have picked up from this article, making boots resoleable tends to produce the kind of stiff and heavy builds that a lot of people find uncomfortable.

If you’re OK with boots that won’t last through multiple soles but still manage to be pretty water resistant, check out the classics from Timberland, Blundstone, and Dr. Martens.

Conclusion

Well, that was a pretty complicated answer to “what’s the most comfortable boot,” but that was ten ways of approaching that question and a whole lot of brands that can help. I hope you leave with more focus than confusion — that was my goal here, believe it or not!