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: Koio’s Trento, $365
• The Best Men’s Moc Toe Boot: Grant Stone’s Brass Boot, $360 – $395
• The Toughest Boot: White’s MP Sherman, $650 – $670
• The Luxury Dress Boot: Alden’s Indy, $660
• Warmest Winter Boot: Sorel’s Caribou, $200
• Most Comfortable Cowboy Boot: Chisos No. 2 Square Toe Boots, $592
• Best Desert Boot: Clarks Desert Boots, ~$110
• Best Waterproof Hiking Boot: Danner 453 Gore-Tex, $240

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’s Captain Boot

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.
• Light weight: If you prefer the feeling of a bulky, stompy work boot, this ain’t it; the Captain is more suited for city wear.

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 lets them produce a marvelous boot for just $199.

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 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
• $442 – $480

2) Best Men’s Chelsea Boots: Koio’s Trento

What I like:

• Value: They’re Italian made, and wearing sustainably produced leather adds to the value, in my opinion.
• Comfort: I like the flexible, lightweight construction and comfy leather soles; they quickly felt custom-fitted to my feet.
• Quality: I prioritize buying resoleable boots; these are Blake stitched and resoleable.
• Aesthetics: The sleek profile and lack of chunky welt stitching are minimalist but not too dressy, which I love.

What I dislike:

• Quality: Blake stitching is resoleable, but there are a limited number of times you can do it.
• Fit: The biggest downside is that there are no half sizes nor wide widths, but the best hack for loose Chelseas is this $10 tongue pad. Total game changer.

The Trento is simply a boot that gets it right: stellar materials, versatile design, and nothing unnecessary.

What I love about this boot is its commitment to classic Chelsea construction. While I often gravitate to hardy Goodyear welts and luggy Commando soles, Koio went with the classic European combination of Blake stitch and leather sole.

What that means is comfort: a more flexible, lightweight boot than most of the ones that populate the market today, yet it’s still completely resoleable.

While this city boot isn’t as well suited for trudging around a forest as some, the all-leather construction will do a great job conforming to the foot over time and giving you a boot that feels custom fitted to you.

The only problem is selecting a leather: a smooth black that can easily be worn with a suit or a smart casual suede.

[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: Grant Stone’s Brass Boot

What I like:

• Value: For a high end boot, I think these are a solid value at $360 – $395, depending on leather.
• Comfort: I like the roomy toe and unusual array of widths.
• Quality: From Horween Chromexcel to CF Stead suede, these feature the world’s best leathers.
• Fit: These have a roomy but secure fit; my feet felt great.
• Aesthetics: More versatile than most moc toes, I liked how the classic casual style really elevates any informal outfit.

What I dislike:

• Function: Many people wear moc toes for work. You should know these are better suited for casual wear.
• Price: The value comes from the quality control and high end materials; the average guy may not find those compelling reasons to pay over $350.

Next up is the best moc toe boot, an absolutely classic casual style that really elevates any informal outfit.

Grant Stone’s Brass Boot is a unique, very versatile boot from a company better known for making smart casual footwear — the Brass Boot is their first attempt at a work boot style boot.

These aren’t made for electricians or anyone working in hazardous situations, but it’s roomy, it’s sturdy and muscular, and they go great with casual clothing.

The moc toe is a classic casual boot style. But this moc toe is just a little sleeker than your average moc, and I’ve found they pair as well with a button-down and a blazer as with old blue jeans and a t-shirt.

The Brass Boot’s leathers are spectacular quality (this golden one is Italian vegetable-tanned leather that will age beautifully), and it’s a great pick for guys who want one boot that can pair with almost anything.

[Related: Best Selvedge Denim for Men]

Runner Up: Red Wing’s Classic Moc

• American made
• Iconic aesthetic
• $299

4) Toughest Boots: White’s MP Sherman

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

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.

Runner Up: Truman Boot Company

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

5) Best Men’s Luxury Boots: The Alden Indy

What I like:

• Value: I love that it is made in New England with top-notch materials.
• Comfort: They live up to their reputation as incredibly comfortable for all-day wear.
• Quality: A storm welt for extra water resistance is greatly appreciated.
• Fit: They come in more widths than almost any other brand, from B (extra narrow) to EEEE (extra, extra, extra wide).
• Aesthetics: Worn by Indiana Jones, but I don’t think they make you like a dowdy professor.

What I dislike:

• Price: I don’t love the almost-$700 price tag, but the materials and labor justify the cost.
• Heel: The comfy rubber heel is known to wear down somewhat quickly. (But it’s easy to replace)

“Luxury boot” doesn’t necessarily mean “dress boot;” you can wear everything on this list casually. I’m talking about leather boots that are truly legendary in the industry for their history, their quality, and, sure, for their price. Both leather boots in this section come from companies founded in the 19th century, costing well over $500.

The first is the Alden 403, better known as the Indy, because this is the boot Indiana Jones wears in all his movies. If that’s not the coolest hook ever, I don’t know what is.

The low profile design is unique and eye-catching, yet subtle. The boot also has a storm welt for extra water resistance and protection against the elements, plus Alden makes them in New England from start to finish.

Podiatrists often recommend the Indy for people with foot pain because their last is famously supportive — the brand has a history in orthopedics. It’s especially evident when I’m on my feet all day. And especially when I need to survive a nuclear explosion in a fridge.

Runner Up: Carmina’s 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

What I like:

• Value: At under $200, 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.

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 $200, these are more than enough.

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
• $478

[Related: 20 Best American Made Boots to Buy in 2025 (Made in USA!)]

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

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 held preserve Texas’ natural spaces.
• Value: The price isn’t low but 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.

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 nature conservancy.

The No.2 is a classic styled cowboy boot with an 11” shaft and a not-too-high one 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’ 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.

My Clarks Desert Boot YouTube Review

8) Best Men’s Desert Boots: Clark’s Desert Boot

What I like

• Comfort: Very lightweight and flexible.
• Aesthetic: Excellent casual boot, great for wearing with jeans. These are not dress boots.
• Value: Excellent price for the suede quality and comfort.

What I dislike

• Not very durable: The construction won’t handle a resole, and the soft sole wears down fast.
• Not versatile: It’s a firmly casual boot but hey, that’s chukkas.

Widely considered the default starter boot for guys looking to start dressing well, Clarks desert boots are comfortable, lightweight, casual classics in a huge range of leathers, suedes, and even canvas.

The crepe sole is extremely soft and flexible, the suedes come from Britain’s world-famous CF Stead, and the price is impressive.

It’s neither the best-looking nor strongest-wearing boot I own, but it’s not meant to be some super durable logger boot. It’s a basic, simple boot and very informal.

Runner-Up Thursday Scout Chukka Boots

• Much more durable than Clarks
• Sturdy underfoot
• $199

9) Best Men’s Hiking Boots: Danner 453 Gore-Tex

What I like

• Comfort: Famously lightweight and supportive
• Fit: I like that it comes in wide and half sizes, which is imperative for hiking wear.
• Quality: The waterproof Gore-Tex lining is a hiker’s best friend.

What I dislike

• Durability: Not resoleable nor “recraftable,” but Danner is upfront about this.

The best waterproof hiking boot is the Danner Mountain’s 453. This longstanding Pacific Northwest boot brand has a reputation for making really durable hiking boots, and it has the strongest cult following.

Danner has worked with Gore-Tex for decades and knows just how to make boots that are both waterproof and breathable, plus they added a scuff-proof toecap for durability and an innovative outsole that emphasizes downhill breaking and side hill traction.

They’re a bit too technical looking for everyday wear, but the combination of value and function is ideal.

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 twelve 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. Whether you prefer desert boots, hiking boots, cowboy boots, or ankle boots—  just make sure you do your due diligence before buying a pair and make sure it is worth the money!