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I’m continually surprised by how many bad boots are on the market. Think about it: this footwear needs to go from concept to capital to production with hundreds of steps along the way. Companies need to be formed. Leather needs to be tanned. Websites need to be created. Entire businesses are formed around products that are just plain bad.
There are countless things that can go wrong with a boot and I’ve seen them all: iffy arch support, slippery soles, lousy lasts… and then there are the issues that you can’t pick up on when you’re trying boots on in a store, likeleather that creasestoo fast orheels that detachafter just a few weeks. And no matter how many boots I own — and I own well over a hundred pairs — I always gravitate toward a small group of favorites.
Enough is enough. I’m sick of seeing men doing their feet a disservice. So today, I’m going to unveil the best boots for men to buy in 2023. Out of every boot I own, these are my ten all-time favorites.
Table of Contents
What Makes The Best Boots? My Criteria For Selecting These 10 Boots
Before the list of the best boots, I wanted to start off by sharing the criteria I used in making my selections.
The main factors I looked at were value, comfort, quality, fit, and aesthetics. Together, I feel that these five variables make up a fair representation of the best boots. Let me quickly explain my thought process behind each of these:
- Value: When it comes to boots, you almost always get what you pay for. With that said, you can consider value instead: this speaks to what you get compared to what you pay. If I say a boot has great value, it means the brand could be charging more for the quality they’re offering.
- Comfort/Fit: Of course, the best boots need to be comfortable. Whether you wear them for a few hours or the entire day, you want your boots to be soft yet supportive, ideally with a measure of shock absorption. Oftentimes, you won’t even notice you’re still wearing the most comfortable boots!
- Quality: The best boots are more or less synonymous with the highest quality boots — at least, to a certain point. The materials used should be premium, and the boot needs to be built to stand the test of time.
- Aesthetics: Finally, I considered the aesthetics that a boot provides. This is all about appearance, and sure, it may be a bit surface level — but the best part about building out your collection is having a boot for every occasion!
Do you want to learn more about my criteria when I rank boots? Check out our 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 officially ready to unveil my #1 pick with you: The Thursday Boot Company’s Captain Boot.
[Related: My list of TheBest Leather Briefcases for Men]
1) Best Boot: Thursday Boot Company’s Captain Boot
The Best Damn Boot
Thursday Boot Co. Captain Boot
A comfortable, durable, and versatile cap toe boot handcrafted with quality leather from US hides and featuring Goodyear welt construction. The Captain is built to last — and match with anything.
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- Versatile dress/work boot hybrid
- Wide variety of leathers
- Just $199
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 on the market. The average guy doesn’t want to spend over $300 for a pair of boots, but that’s what every solid option on the market costs — except Thursday.
Tired of the premium price of your average resoleable boot, the guys who started this brand went with a direct-to-consumer model that let them to cut out the markups of brick-and-mortar stores and produce a stellar boot for just $199.
The Captain’s M.O. is that it’s the ideal midway point between dainty dress boots and chunky work boots. The result of this design philosophy is a slim-but-not-too-slim boot that dresses up just as easily as it dresses down.
It also has a 360-degree Goodyear welt that’s subtle and close in to the vamp, so while it’s very water-resistant and easy to resole, it doesn’t have the chunkiness that you often get with a full Goodyear welt. Another way it improves on the traditional work boot is a layer of EVA on the insole, a foam that’s often used in sneakers, resulting in a boot that absorbs shock and feels closer to a sneaker than hard-as-nails work boots.
The Captain boot is a wholly unique product that combines dressy and casualin a way no other boot had before they came along. 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 inarguably the best value boot on the market and in my opinion, the best boot, period.
[Further Reading: How to Size Thursday Boots]
Runner Up: Oak Street Bootmakers’ Trench Boot
Simple Yet Luxury
Oak Street Bootmakers Trench Boot
Oak Street might make America's best luxury city boot. Sturdy and durable but not too heavy or casual, it also has a deceptively wide toe box for extreme comfort.
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- Made in USA
- Wide toebox for comfort
- $442 – $480
The runner up for the best boot overall is the Trench boot from Oak Street Bootmakers.
These are beautiful leather boots with really robust construction. They’re made in Chicago with leather from the city’s famous tannery, Horween Leather Company. It’s a really sturdy, versatile, and resoleable boot with extra thick leather in the upper and sole, and it has the kind of design simplicity that lets the construction and materials speak for itself.
It’s also totally made in America (even the packaging is sourced domestically), but at about $460 it’s not cheap, so it’s hard to recommend for everyone. They go on sale several times a year, though, and if you’re happy to get one with a leather sole then the boot is about twenty bucks cheaper.
2) Best Chelsea Boots: Koio’s Trento
20% OFF
Koio's Trento Boot
With a flexible, lightweight construction that remains water resistant and resoleable, this sleek Chelsea hits all the right notes — in three colorways to boot.
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- Flexible, lightweight construction
- Comfy leather soles
- Sustainably produced leather
The Trento is simply a boot that gets it right: stellar materials, versatile design, and no unnecessary features.
What we love about this model is its commitment to old fashioned construction. While a lot of folks prefer hardy Goodyear welts and luggy Commando soles, Koio went with the classic combination of Blake stitch and leather soles. 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.
Comfort is the name of the game, here. While this city boot isn’t as well suited for trudging around a forest as some, the all-leather construction makes for a Chelsea that will do a great job conforming to the foot over time and giving you a boot that feels custom fitted to your feet.
The only problem is selecting a leather: a smooth black that can easily be worn with a suit, or one of their more smart casual suedes?
Runner Up: R.M. Williams Comfort Craftsman
Wolverine's Favorite
R.M. Williams' Comfort Craftsman
The world famous Australian classic, this boot is endorsed by Hugh Jackman himself and is made with a supple yearling leather that combines the best of calf and cowhide.
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- Made in Australia
- Yearling leather is a great balance of soft and tough
- Versatile aesthetic
- ~$550
Chelsea boots are a fundamental part of any guy’s wardrobe and the best has to be R.M. Williams.
It stands out in the market for two main reasons. The first is that it’s whole cut, meaning the upper is made of just one piece of leather that wraps around the foot and stitches together at the ankle. This makes for a supremely comfortable fit that does a better job than other Chelseas at molding to the foot, becoming almost “sock like” with time.
The second reason is that it’s made with unusual “yearling leather,” sourced from one-year-old calves. This gives it the best of both worlds: it’s tough and hardwearing like cowhide, but soft and with a fine grain like calfskin.
Not everyone likes the slightly square toe but they’re insanely comfortable (I sometimes forget to take them off when I get home), they last forever, and Hugh Jackman does their commercials, so ~$550 may be perfectly justifiable for you.
3) Best Moc Toe Boot: Grant Stone’s Brass Boot
The Best Moc Toe
Grant Stone’s Brass Boot
With world class leathers, muscular construction, versatile good looks, three widths, and a variety of premium uppers and soles to choose from, this is our favorite moc on the market.
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- More versatile than most moc toes
- High quality, Italian vegetable tanned leather
- $330 – $380, depending on leather
Next up is the best moc toe boot, an absolutely classic casual style that really elevates any informal outfit. The Brass Boot from Grant Stone is a completely unique, very versatile boot from a company that’s better known for making really nice footwear that’s a bit more dressy than this — the Brass Boot is their first attempt at a work boot type boot.
That might not mean it’s perfect for electrician work so much as it means it’s roomy, it’s sturdy, it’s muscular, and it goes great with casual outfits. But this moc toe is just a little sleeker than your average moc, and I’ve even seen guys say they can wear them with button-downs and a blazer just as easily as with old jeans and a t-shirt.
The Brass Boot’s the leather is spectacular quality (this golden one is Italian vegetable tanned leather that will age beautifully) and it’s a great pick for guys who don’t own a lot of boots and want one pair that pairs well with almost anything.
Runner Up: Red Wing’s Classic Moc
The American Icon
Red Wing Classic Moc
This may be America's most iconic boot. Build the same way since the 1950s, this boot is equally at home on the jobsite as it is paired with modern streetwear.
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- American made
- Iconic aesthetic
- $299
The runner up is Red Wing’s Moc Toe, which is the moc toe of moc toes. My Charcoal onesare my oldest pair of boots and they’re absolute classics. Everyone from Ryan Gosling to Drake has a pair, usually in the golden Oro Legacy leather that matches with practically everything.
I prefer the Brass Boot because of its leather quality and, again, I think the silhouette is more versatile — you simply cannot dress up a Red Wing moc toe — but Red Wing’s is cheaper at $299, plus it’s made in the USA.
4) Toughest Boots: White’s MP Sherman
The Toughest Boot
White's Boots' MP-Sherman
The MP Sherman is tough as nails yet not too chunky or bulbous, as it's modeled after boots worn by WW2 infantrymen rather than work boots. But rest assured, it can handle anything you throw at it.
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- Handsewn stitchdown construction
- Very thick, tough leather
- Modeled after military police boots
- $650 – $670
It’s important to note that I’m not looking at boots that can withstand magma or lightning, rather boots that look great when worn out on the town and are still tough as nails when they need to be. For that, I had to go with White’s.
Made with a leather upper, midsole, and insole about twice as thick as you find in cheaper brands, the boots are so substantial you’d swear you’re wearing a cow on either foot. But it’s not just the weight that matters to purists: these boots are made with handsewn stitchdown construction, which is far more laborious and time-consuming for craftspeople than the standard Goodyear welt found on the other entries on this list. Many find it makes for a more comfortable boot overall, and when that’s combined with the timeless aesthetic and world class leathers, White’s cannot be beaten.
For guys who appreciate craftsmanship, durability, and made-in-USA goods, head to White’s.
Runner Up: Truman Boot Company
The Coolest Leathers
Truman Boot Co. Coach Rambler
Truman's boots are made in Oregon with super robust construction and the widest variety of unusual, colorful leathers you'll ever find on rugged footwear like this.
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- Made in Oregon
- Wide range of cool, unique leathers
- $399-$520
An all-American brand founded in Pennsylvania and now based in Oregon, Truman Boot Company stands out in the marketplace for the chunky, rugged design and their very creative leather selection.
More bulbous and work boot-y than the MP Sherman above, Truman — depending on availability — has the most innovative leathers in the game, from bright red to sky blue, deep green, and more.
My own boots are made with the company’s flagship Java Waxed Flesh, a roughout leather from Horween that’s ultra-durable and scratch-resistant, and it ages beautifully, lightening over time and revealing a golden nap underneath.
When I wear a pair of Truman boots I feel indestructible and, well, cool. There, I said it.
5) Best Luxury Boot: The Alden Indy
The Dressed Up Adventurer
Alden Indy Boot
Alden's Indy Boot is a Goodyear welted staple in the heritage boots scene. This iconic boot was Harrison Ford's boot of choice when he filmed the Indiana Jones series.
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- Extraordinarily comfortable
- Made in New England
- Worn by Indiana Jones
- $600-$690
“Luxury boot” doesn’t necessarily mean “dress boot;” everything on this list can be worn 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 and both cost well over $500.
The first is the American-made 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.
It’s a really cool design that’s unique and eye-catching, yet subtle. The boot also has a storm welt for extra water resistance (handy when you’re swimming onto German U-boats), plus Alden makes them in New England from start to finish.
Founded in 1884, the company has a surprising history of making orthopedic shoes. That emphasis on anatomic correctness may be why they come in more widths than almost any other brand, from B (extra narrow) to EEEE (extra, extra, extra wide).
The Indy is often recommended by podiatrists for people with foot pain because they’re such comfortable, supportive shoes. Especially if you’re on your feet all day. And especially if you need to survive a nuclear explosion in a fridge.
Runner Up: Carmina’s Chelsea
The Suit Chelsea
Carmina's Simpson Chelsea
Founded 1866, Carmina has a world class reputation for delicately lasted dress boots with surprisingly durable and flexible construction.
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- Made in Spain
- Luxurious French box calf leather
- Three layers of leather in the sole for softness underfoot
- ~$525
The next best luxury boot is Carmina’s Chelsea Boots. This is a Chelsea boot with a very rich history: it’s made on the Spanish island of Mallorca and the family’s history of shoemaking there stretches back to 1866. In fact, we visited Mallorca ourselves to find out just how Carmina boots are made.
The company is well known for their elegant lasts. A few highly regarded aspects are that the upper is made with box calf leather, a celebrated French calfskin that’s known for its smoothness and vibrance; the sole is three layers of leather, which many consider the ideal construction for softness and comfort; and there are many interesting touches from their precision craftsmanship like the sole’s high stitches per inch and closed channel stitching.
Wrapping Up My List Of The Best Boots
Well, there you have it: the best boots 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 ten and while I believe any of these would be a great addition to a man’s wardrobe, I believe Thursday’s Captain Boot is the best overall.
But that’s just me. Everyone has their own preferences, and I’m confident that the perfect boot is waiting for you on this list. Whether you prefer Chelsea 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!
