16 Best Boots For Men to Buy Tested By Experts (Spring 2025)

I own well over a hundred pairs of boots; I’ve traveled the world to find the best boots for men. I’ve interviewed experts, including bootmakers, cobblers, and other collectors. Collectively, I’ve walked hundreds of miles in these boots, so I’ve got a pretty good handle on what makes a quality boot.

Reviewing boots has also literally been my job for over five years now. I’m a fanatic. Here, you benefit from my madness.

Best Men’s Boots Buying Guide

• The Best Men’s Boot Overall: Thursday Captain Boot, $199
• The Best Men’s Chelsea Boot: Meermin Mallorca Wholecut, $280
• The Best Men’s Moc Toe Boot: Red Wing Heritage Classic Moc, $330
• The Toughest Boot: White’s MP Sherman, $750
• The Luxury Dress Boot: Allen Edmonds Park Ave, $550
• Warmest Winter Boot: Sorel Caribou, $250
• Most Comfortable Cowboy Boot: Chisos No. 2 Square Toe Boots, $595
• Best Desert Boot: Astorflex Brownflex, $250

No matter how many boots I try, I always gravitate toward a small group of favorites.

So today, I’m going to unveil the best boots for men to buy in 2025. Out of every boot I own, these are my twelve all-time favorites.

What Makes The Best Men’s Boots? My Criteria For Selecting These Boots

When you wear new boots as frequently as I do and build a sizeable boot collection, you eventually hone your criteria to a few deal breakers. Cheap leather, nah. Cracking soles, get out of here. Make me look uncool, not my thing.

I wear each boot for at least a month, averaging about 16 miles of wear time. The main factors I look at are value, comfort, materials, construction, fit, and aesthetics.

Together, these six variables make up a fair representation of the best boots. (Check out my boot review process for a more in-depth understanding.)

Now that you know what I had in mind when compiling this list of the best boots, I’m ready to unveil my #1 pick: Thursday Boot Company’s Captain Boot.

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

1) Best Men’s Boots Overall: Thursday Boot Company Captain Boot

Out of my eye-wateringly huge collection, the Captain is the boot I always recommend. It simply has the best combination of value and versatility.

I don’t always love spending over $300 for a pair of boots, but that’s what practically every good boot costs — except Thursday. Their direct-to-consumer model and mastery of boring supply chain logistics let them produce a marvelous boot for just $199.

What I like:

• Value: At just $199, this is the best value boot I own.
• Comfort: My feet love the cushioning from the EVA foam insoles.
• Quality: I dig the resoleable and water-resistant Goodyear welted construction.
• Fit: Fits perfectly without squishing the toes, plus they have sizes from 6 – 16 and wide widths.
• Aesthetics: A versatile hybrid of dress and work boots that comes in a wide variety of leathers.

What I dislike:

• Less leather: Instead of a traditional leather insole, Thursday uses EVA foam. This is much better at shock absorption, but some guys prefer all leather construction.
• Lightweight: If you prefer the feeling of a bulky, stompy work boot, this ain’t it; the Captain is more suited for city wear.

The Captain’s M.O. is that it’s the midway point between dainty dress boots and beefy work boots. This design philosophy results in slim-but-not-too-slim cap toe boots that dress up as easily as they dress down. If you don’t like the cap toe, I’ve reviewed Thursday’s plain toe boot called the President. I think cap-toe boots are a bit more casual, while plain-toe boots are a bit dressier.

This boot has a 360-degree Goodyear welt (unheard of at this price), making it very water-resistant and easy to resole, while avoiding the chunkiness you often get with this construction.

Another way it improves on the traditional work boot is that the insole has a layer of EVA, a foam often used in sneakers, producing a boot that absorbs shock and feels closer to a sneaker than hard-as-nails work boots.

The cherry on top: it’s so popular that it comes in over a dozen leathers, so you’re guaranteed to find something you like. It’s unarguably the best value boot on the market.

[Further Reading: How to Size Thursday Boots]

Runner Up: Oak Street Bootmakers Trench Boot

• Made in USA
• Wide toebox for comfort
• $462 – $488

2) Best Men’s Chelsea Boots: Meermin Mallorca

Chelsea boots are great, but they have a glaring problem: no laces with which to adjust the fit. This means that it’s easier for a Chelsea just not to fit your foot, no matter how much you like them.

And I’m not talking about the fact that some guys need wider sizes: with Chelseas, you’ll find that your instep height, ankle width, and fit issues you never knew you had will come into play.

That’s why Meermin deserves the top spot for selling their famous Chelseas in four different lasts: dressier Rod, wider-heeled Hiro, chiseled Orion, and the wide-forefoot Negon — my personal favorite, as it accommodates my low instep.

What I like:

• Value: All resoleable and all under $300 is commendable, but especially for wholecut boots.
• Comfort: Sold on three different lasts, so you have more control over fit than you usually do with laceless boots.
• Quality: They offer different kinds of builds, including storm welts with lug soles and uncommon “Flex” Goodyear welts with recessed grip — all resoleable
• Aesthetics: The brand is best known for their wholecut pattern: it’s just one piece of leather stitched behind the heel, making a gloriously minimalist boot

What I dislike:

• Aesthetics: Limited leathers; everything is brown or black at the moment.
• Fit: They use UK sizing, which is tricky.

It’s rare to find a wholecut Chelsea, but it’s recognizable by the lack of seams under the elastic goring on the side. In other words, it’s one piece of leather wrapping around the whole foot, which means it has a very “clean” aesthetic, plus some find it more comfortable.

Lastly, all their Chelseas are resoleable, but they have several unusual ways of approaching the Goodyear welt to make it more comfortable: some have more flexible soles, some swap the cork filling for foam, some go traditional.

I recommend them, but first find a shoe salesman to ask if there’s anything unusual about your foot’s dimensions. Then pick the last that’s right for you. Every Chelsea brand should do this; no one but Meermin does it anywhere near this price.

[Check Out: The 10 Best Loafers for Men]

Runner Up: R.M. Williams Comfort Craftsman

• Made in Australia
• Yearling leather is a great balance of soft and tough
• Versatile aesthetic
• ~$550

3) Best Men’s Moc Toe Boots: Red Wing Heritage Classic Moc

It’s impossible to overstate the impact Red Wing’s Classic Moc has had on the industry. The brand was founded over a hundred years ago in Minnesota, which is where its range of “heritage” casual boots is still made to this day.

What I like:

• Value: For a resoleable American-made boot of this quality, it’s hard to beat $330.
• Comfort: I like the roomy toe and bouncy sole.
• Quality: Red Wing owns their own tannery and factory, meaning they have a lot of control and oversight of the product’s quality.
• Fit: I love the roomy fit and high side walls of this casual last.
• Aesthetics: Red Wing’s design is very famous, works with a range of styles, and comes in 10+ leathers at a given time.

What I dislike:

• Comfort: Expect a tough break-in with leather this hefty.
• Versatility: These can’t be dressed up even a little.

Originally conceived of as a hunting boot, the Classic Moc’s stability and durability led it to become a staple of jobsites while its classic good looks ultimately made it America’s most recognizable casual boot — yep, I’m standing by that.

Best known for the 875 model that’s made with the iconic, golden orange Oro Legacy leather, you’ve probably seen a lot of orangey moc toe boots that resemble the 875, but know that this is the original.

Often the first good boot an American male buys (it was for me), the Classic Moc has a famously tough break-in period, but its balance of style, durability, (eventual) comfort, and value can’t be beat.

I know that $330 sounds like a lot of money, but by owning their own factory and tannery, Red Wing has managed to beat the prices of most American-made boots of this kind of quality.

Runner Up: Grant Stone Brass Boot

• Very premium leathers
• Famously exacting quality control
• Three widths available
• ~$435

4) Toughest Boots: White’s MP Sherman

I’m not looking for boots that can withstand magma or lightning, but boots that are still tough as nails when needed and look great when out on the town. For that, I had to go with White’s.

Made with a leather upper, midsole, and insole about twice as thick as cheaper brands, the Shermans are so substantial you’d swear you’re wearing a cow on either foot.

But the build quality might matter more: these boots are made with handsewn stitchdown construction, which is far more laborious and time-consuming to craft than the standard Goodyear welt found on the other entries on this list.

When that’s combined with the timeless aesthetic and world-class leathers, White’s cannot be beaten.

What I like:

• Value: I think they’re a fair price for a boot handmade in the USA with top-tier construction
• Comfort: I really liked how they contour to my feet, and the arch support is great
• Quality: Handsewn stitchdown construction is very skillful
• Aesthetics: They’re modeled after military police boots, which are sleek yet masculine

What I dislike:

• Price: $650 – $670 is a lot to pay for a boot, even if they are very well-made.
• Comfort: I like the durability, and these are comfy, but the thick materials are heavier than other casual boots out there

Runner Up: Truman Boot Company

• Made in Oregon
• Wide range of cool, unique leathers
• $399-$520 

5) Best Men’s Dress Boots: Allen Edmonds Park Ave

Founded over a hundred years ago in Wisconsin, Allen Edmonds is one of the last remaining bastions of American leather footwear, and they’re probably best known for two things: their incredible range of widths (there are nine to pick from here) and their Park Avenue boot.

What I like:

• Value: For a resoleable, American-made boot with high-end French calfskin leather, under $600 is a decent deal.
• Comfort: I’m a huge fan of the leather soles: they’re not just dressy, they offer a unique balance of softness and stability.
• Quality: Goodyear welted for durability while staying sleek enough for professional wear.
• Fit: Next to no one approaches the nine widths Allen Edmonds offers off-the-rack
• Aesthetics: Balmoral style with Oxford lacing and blind eyelets: this ticks all the boxes of a dress boot.

What I dislike:

• Performance: I love them, but some guys can’t be convinced to wear leather soles.
• Comfort: They didn’t use a leather midsole so as to keep the boot low profile and professional looking; some might miss the stability of a midsole.

Often called “a man’s first dress shoe,” Allen Edmonds has sold over two million pairs since it debuted in the 80s, and when they released it in boot form, it immediately became the most obvious pick for a dress boot.

There are a few elements that make it “definitely a dress boot”: the Balmoral pattern (note the horizontal seam running along the quarter), blind eyelets (you can’t see the metal reinforcing them), and Oxford lacing (the facings don’t close over the boot like derbies do; they’re instead under the vamp).

The leather sole and calfskin uppers, while not unique to dressy footwear, definitely underscore the Park Avenue’s formality.

That all might sound a bit complicated, but you can just trust me: many boots claim they can be dressed up, but Allen Edmonds’ Park Ave boot is the only model that has both the stylistic criteria and the undeniable legacy of business professional footwear.

Runner Up: Carmina Chelsea

• Made in Spain
• Luxurious French box calf leather
• Three layers of leather in the sole for softness underfoot
• ~$525

6) Best Men’s Winter Boots: Sorel’s Caribou

For winter, we’ve got Sorel’s Caribou boots, one of the most famous winter boot brands. Dedicated, insulated, waterproof winter boots tend to be, well, hideous, but Sorel’s is the best-looking snow boot on the market.

And they get the job done.

They’re insulated with recycled felt and Sherpa pile and fully waterproof. I wouldn’t work all day in the cold, but they’re great for casual wear — and if you’re looking for slightly more fashionable winter boots that work as everyday wear for under $250, these are more than enough.

What I like:

• Value: At $225, there’s no sticker shock here.
• Comfort: Out-of-the-box comfort, plus they’re insulated and waterproof.
• Quality: I liked how the “Ero-Trac” sole keeps snow from compacting in it.
• Fit: These are very lightweight for such functional footwear.
• Aesthetics: Compared to a lot of chunky winter boots, I think these look pretty good.

What I dislike:

• Durability: These aren’t resoleable, but that’s common for waterproof boots.
• Aesthetics: It’s not a timeless leather boot, but it’s better looking and performing than most alternatives.

Runner Up: Rancourt’s Freeman

• Lined with toasty shearling
• “Arctic Grip” soles are excellent on snow and ice
• Made in the USA with premium American leather
• $498

7) Best Cowboy Boots: Chisos No. 2 Square Toe Boot

Chisos Boot Company is admirable, emphasizing ethics and transparency at every level while making the most comfortable Western boots I’ve tried. I love that the leather comes from retired dairy cows instead of calfskin and their charitable donations to the Nature Conservancy.

What I like

• Quality: Excellent, small shop craftsmanship. They are resoleable.
• Comfort: Extremely comfortable; this is best-in-class, sneaker-like comfort out of the box.
• Fit: Incredible arch support.
• Transparency: I like that a portion of sales is held to preserve Texas’s natural spaces.
• Value: The price isn’t low, but it aligns with the quality.

What I dislike

• Leather soles. They aren’t the grippiest in the rain, but their breathability makes them the sole choice for cowboys.

The No.2 is a classic styled cowboy boot with an 11” shaft and a not-too-high 1 ⅝” heel. The arch support is outstanding, the insole absorbs shock, and there are countless signs of quality, small shop craftsmanship like hand-channeled-welts and stitch designs inspired by petroglyphs found in Texas’s Chisos Mountains.

I also love the fit: your foot slides into the boot easily and then pops in place. After hours of wear, my feet didn’t feel sore at all.

8) Best Men’s Desert Boots: Astorflex Brownflex

Desert boots are the best way to wear boots in summer. They’re chukkas, a term for short boots with just two or three pairs of eyelets, but desert boots are a subcategory of chukkas with crepe soles and suede uppers.

Originating in South Africa, the breathable suede and soft soles made them the go-to style for guys who miss boots in summer — but they work pretty darn well with smart casual outfits too.

Astorflex is our favorite because they’re well priced for Italian-made and they’re higher quality than your average desert boot: while these models tend to emphasize floppy lightness, the Astorflex Brownflex‘s leather midsole and resoleable build give it a rare balance of sturdy and summery.

What I like

• Comfort: A great balance of durable and lightweight.
• Aesthetic: Suede upper and crepe sole make it an ideal desert boot for warm weather.
• Value: Excellent price for the suede quality and comfort.

What I dislike

• Not versatile: It’s a casual boot, but hey, that’s desert boots for you.
• Fit: I’d prefer they offer half sizes and multiple widths

Runner-Up: Clarks Desert Boot

• Unusually soft sole and thin suede
• Less durable, but closer to a summery sneaker than Astorflex
• $150

Wrapping Up My List Of The Best Boots

Well, there you have it: the best boots for men on the market, as reviewed by someone who owns well over a hundred pairs! I haven’t tried every boot on Earth, but I’m very confident in my picks for the best boots on the market right now.

I took into account value, comfort, quality, fit, and aesthetics to land on these sixteen boots, and while I believe any of these would be a great addition to a man’s wardrobe, Thursday’s Captain Boot is the best overall. 

Everyone has their preferences, but I’m confident that the perfect boot awaits you on this list. No matter if you prefer moc toe, Chelsea, desert, cowboy, cap toe, or something else on this list, you can be glad you’ve done your due diligence before selecting your next favorite pair of boots.