The 10 Best Boots For Men to Buy (Updated for 2021)

I’m continually surprised by how many bad boots are on the market. Think about it: these shoes need 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, like leather that creases too fast or heels that detach after 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 2021. Out of every boot I own, these are my ten all-time favorites.

What Makes The Best Boots? My Criteria For Selecting These 10 Boots

Before I actually get into my list of the best boots, I wanted to start off by sharing the criteria I used in making my selections. That way, you understand where I was coming from and know I didn’t just throw this list together willy-nilly.

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: I don’t like to shop based on price. 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 far more for the quality they’re providing.
  • 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. 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.

1) Best Boot: Thursday Boot Company’s Captain Boot

  • Versatile dress/work boot hybrid
  • Wide variety of leathers
  • Just $199

This is a really phenomenal boot and despite my eye-wateringly huge collection, it’s the one I wear the most.

The guys who started the company were fed up with the fact that most good boots are expensive simply because of the brand’s value and not because of the actual quality of the materials and construction. 

They were also after boots that were neither dainty dress boots nor heavy work or hiking boots — the idea was to make a new kind of boot that you can wear with anything and won’t cost you an arm and a leg. And, in my opinion, they nailed it.

So Thursday’s Captain boot is in no way an imitation of somebody else’s product. It’s a wholly unique product that’s meant to be the perfect hybrid boot, a combination of dressy and casual that I think completely succeeds.

thursday captain boot walking

The shoe 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 any of the chunkiness that you often get with a full Goodyear welt. On top of that (literally) there’s an EVA comfort strip, a kind of foam that’s often used in athletic shoes. It results in boots that, after a few days of breaking in, feel a lot more like a pair of sneakers than quality leather boots.

Perhaps the most remarkable aspect of the boot is the price: $199. This is inarguably the best value boot on the market and in my opinion, the best boot, period.

[Shop the Captain boot in 12+ different leathers here.]

Oak Street boots dangle
See the full review

Runner Up: Oak Street Bootmakers’ Trench Boot

  • Made in Chicago
  • Sturdy construction
  • $420-$470

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 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.

[Shop the Trench boot here!]

grant stone brass boot

2) Best Moc Toe Boot: Grant Stone’s Brass Boot

  • More versatile than most moc toes
  • High quality, vegetable tanned leather
  • $340

Next up is the best moc toe boot, an absolutely classic casual style that really elevates any casual 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 tiny bit sleeker than your average moc, and I’ve even seen guys say they can wear them with button-downs and a blazer as easily as old jeans and a t-shirt.

The Brass Boot is stupid versatile, 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.

[Shop the Grant Stone Brass Boot here!]

red wing 875
Watch the full Red Wing Moc Toe review.

Runner Up: Red Wing’s Classic Moc

  • American made
  • Iconic aesthetic
  • $280

The runner up is Red Wing’s Moc Toe, which is the moc toe of moc toes. My Charcoal ones are 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 $280 to $290 (depending on the leather), plus it’s made in the USA. And if you’re in a pinch, you can even use these as hiking boots!

Whites Service Boot dangle
Watch the full White’s boots review.

3) Toughest Boot: White’s MP Sherman

  • Handsewn stitchdown construction
  • Very thick, tough leather
  • Modeled after military police boots
  • $550 – $600

It’s important to note that I’m talking about the toughest fashion boots, here — I’m not looking at boots that can withstand magma or fire, 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 very thick leather, multiple leather midsoles, and a vegetable-tanned leather shank, 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 demanding than the standard Goodyear welt found on the other entries on this list.

For guys who appreciate craftsmanship and durability, White’s can’t be beaten.

[Shop White’s MP Sherman here!]

truman boot company side view
Watch the full Truman Boot Company review.

Runner Up: Truman Boot Company

  • Made in Oregon
  • Wide range of cool leathers
  • $399-$460

An all-American brand founded in Pennsylvania and now based in Oregon, Truman Boot Company stands out in the marketplace for its spectacular construction, pretty good value (they’re practically all under $460, a good deal for made-in-USA boots), and their leathers.

My 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. But Truman has the most innovative leathers in the game, from bright red to sky blue, deep green, and more.

When I wear a pair of Truman boots I feel indestructible and, well, cool. There, I said it.

[Shop Truman Boot Company here!]

Alden Indy 403 street
Watch the full Alden Indy review.

4) Best Luxury Boot: The Alden Indy

  • Extraordinarily comfortable
  • Made in New England
  • Worn by Indiana Jones
  • $550-$590

“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 as well, and 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.

[Shop the Alden Indy here! Head here if you need wide/narrow widths]

Carmina Chelsea Boot with a suite
Watch the full Carmina Chelsea review.

Runner Up: Carmina’s Chelsea

  • Elegantly made in Spain
  • Luxurious French box calf leather
  • ~$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.

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.

These high end components can be seem a little complicated for the average joe, but I go into more detail in my full review. Suffice it to say,  the Carmina’s Chelsea Boot is widely considered to be very good value at $525.

[Shop the Carmina Chelsea here!]

RM Williams Craftsman grate
Watch the full R.M. Williams Comfort Craftsman review.

5) Best Chelsea Boots: The R.M. Williams Comfort Craftsman

  • Made in Australia
  • Yearling leather is a great balance of soft and tough
  • Versatile aesthetic
  • ~$500

Chelsea boots are a fundamental part of any guy’s wardrobe and the best has to be R.M. Williams. Now, you might think I’m biased because I am Australian and every single Australian owns a pair of these boots, but they have a solid reputation here in the United States as well.

The yearling leather is a great mixture of soft and tough, and I’d say it’s the most versatile Chelsea boots you can get. It’s not uncommon to see them worn with a suit in Australia, which is where they are proudly made; in Manhattan dressing up Chelsea boots is a tad more controversial, but these boots can definitely be worn with a t-shirt or with a blazer.

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 ~$500 really isn’t that much when you think about it.

[Shop the R.M. Williams Comfort Craftsman!]

taylor stitch ranch boot steps
Watch the full Taylor Stitch Ranch boot review.

Runner Up: Taylor Stitch’s Ranch Boot

  • Extra water resistant construction
  • Robust, casual aesthetic
  • ~$350

The final boot on this list is also the most underrated: the Ranch leather boots from Taylor Stitch.

Taylor Stitch is a clothing brand, not a dedicated footwear brand so that might be why everyone slept on this boot upon its release — but it’s really solid. The design is great, the leather is tough, the sole is grippy, there’s some firm but supportive foam in the insole, and the boot has a storm welt like the Alden Indy for extra water resistance.

They’re simply terrific daily beaters, a hair more rugged looking than R.M. Williams but much cheaper.

[Shop the Taylor Stitch Ranch boot!]

Wrapping Up My List Of The Best Boots

Well, there you have it – the best boots of 2021 as reviewed by someone who owns more boots than I’d like to admit! 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 five and while I believe any of these would be a great addition to a man’s wardrobe, I firmly believe Thursday’s Captain Boot is the best of the five.

But, that’s just me. Everyone has their own preferences, and I’m fairly 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! 

The following two tabs change content below.
By day: Manhattan-based journalist with reporting experience on four continents, published in Vice, Men's Health, Popular Science, and a bunch of other places.By night: ravenous consumer of anything and everything related to high end men's boots.Stridewise is where I nurture a maniacal obsession with footwear and share my findings. Say hey: [email protected]