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13 Best Boots for Men: I’ve Hand-Tested Over 100 Pairs

William Barton

Boots, Leather, Heritage Fashion, Denim, Workwear

William founded BootSpy in 2020 with a simple mission: test and review popular men’s boots and give a real, honest opinion. Since then, we've welcomed over 5 million readers on our boot reviews and boot care guides. Reach out to him for your own personalized boot recommendation at william@bootspy.com. Or join 50,000+ subscribers on the BootSpy YouTube channel, or send him a message on the BootSpy Instagram. Read full bio.

Last Updated: Apr 3, 2024
4 min read

I’ve bought, tested, and reviewed over 100 pairs of boots. I’m a professional boot reviewer, here and on my YouTube channel. It’s literally all I do.

This is my current list of the best boots for men for each key category, updated for winter 2024. Regardless of your budget, you’ll find a boot worthy of your investment here.

How Did I Come Up With My List?

  • I’ve reviewed over 100 pairs of boots from many of the most reputable boot brands.
  • Every boot I’ve reviewed I’ve purchased with my own money. I’m not beholden to any boot brands, as explained in my review process guidelines.
  • I’ve visited and toured inside the factories of some of the world’s best bootmakers.
  • My BootSpy YouTube channel has over 50,000 boot fans constantly updating me on new releases and giving me feedback.
  • I’ve been professionally reviewing men’s boots for over 3 years. It’s literally the only thing I do.

I’ve tested duds, and I’ve tested gems. 

This list is the culmination of those countless hours. 

Unlike other “best of” lists, I’ve worn every single one of these boots and tested them out. And I’ve tried their competitors, too, so I know how they compare. 

Later in this article, I also share what some other experts in the boot world consider their favorite boots, so you don’t have to just take it from me only.

5 Test Criteria I Used to Hand-Pick These Boots

My video shortlist of the 11 best boots in 2023

To narrow down this list, I considered these five factors:

  1. Style
  2. Material Quality
  3. Construction
  4. Price
  5. Uniqueness (or X factor)

To me, the best boots use high quality leather, are built to last, pack decent value for money, and don’t look like every other boot out there.

If you want the same, you’re in the right place.

My Recommendations

Best Under $200
Thursday Boots Captain arizona adobe rugged and resilient leather
Thursday Captain
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Price $199
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Boot Type Service
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Suited For Casual
What I Like
  • Goodyear welt construction is durable and water resistant.
  • The variety of leather options and sizing is excellent, plus they ship quickly and customer service is solid.
  • The style: they’re rugged but still slim and modern.
What I Don’t Like
  • The Poron insoles are super comfortable, but less durable than leather (but also less expensive).
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The Thursday Captain is the first boot that launched my obsession, and I know I’m not alone. And I still wear mine often, even though I have over 40 pairs, and many of them cost more. In fact, I resoled and still wear my first pair I bought over five years ago.

The Thursday Captain, with its Goodyear welted construction and wide variety of tough and stylish leather options, is a fantastic boot. And the fact that it’s under $200 makes it a no-brainer if you’re looking to invest in high quality boots you can wear every day.

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The Thursday Captain is where I started my boot obsession. For under $200, you’re getting a Goodyear welted construction, great quality leather, and a comfortable boot you can walk for miles in.

I love the slim, modern styling, but it’s not really a dress boot—the cap toe gives it a rugged edge that fits nicely with my style. I’m sure it’d fit your style, too.

With 16 different leather options at the time of writing, plus standard and wide widths available, it’s pretty easy to find the right fit and style.

You can see what my Thursday Captains look like after four years here.

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I interviewed Teik Oh, the founder of the Bootlosophy YouTube channel. Here’s what he has to say about the Thursday Captain:

“The Captain is an excellent entry into quality Goodyear welted boots, but goes well beyond just an introduction. It’s comfortable and breaks in well, and the rugged service boot pattern has been made more sophisticated so that it’s a totally versatile boot for any outfit.”

Read My Full Review of the Thursday Captain Watch my review after four years of wear below:
Best Casual
Grant Stone Diesel profile view
Grant Stone Diesel
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Price $380
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Boot Type Service
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Suited For Casual
What I Like
  • Subtle details like stitching density show that Grant Stone doesn’t cut any corners.
  • The insole is a 3mm piece of vegetable tanned steer hide—it’s durable.
  • Available in legendary Horween Chromexcel leather.
What I Don’t Like
  • Because it’s a plain toe boot, you need to add cedar shoe trees to help it keep its shape.
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If you’re looking to dive into the deep end of boots, the Grant Stone Diesel is one of the best value-for-money picks I can recommend.

While the Diesel runs between $300 and $400 (depends on what leather and sole combination you get), the quality surpasses many well known brands that cost much more than that (*cough, Allen Edmonds, *cough).

I prefer the Diesel in Horween Chromexcel, which is a legendary leather from Chicago—I think the classy shine and rugged durability pair well with the style and construction of the Diesel.

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My go-to boots are either the Grant Stone Diesel or the Thursday Captain. I think of it this way: if Thursday is disrupting the $300 and $400 boot brands, then Grant Stone is disrupting the $500 and $600 boot brands.

The Diesel features a 360-degree Goodyear split welt, Horween Chromexcel leather, and is made with an entirely leather and cork insole and midsole.

I doubt the Diesel would have any difficulty lasting 10+ years with a little love and care. They’re comfortable, have very little break in, and the construction quality is outstanding.

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Grant Stone gets compared often to Allen Edmonds, and many say the quality is better, even though Grant Stone costs about 30% less. In my experience, the same is true.

The superb craftsmanship comes up a lot in reviews of the Diesel.

Best Dress
Beckett Simonon Elliot laces detail
Beckett Simonon Elliot
Get 15% OFF with code Spy15 Buy Now at Beckett Simonon
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Price $259
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Boot Type Balmoral
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Suited For Formal, Business Casual
What I Like
  • Beckett Simonon leather is phenomenal.
  • Blake stitch construction is classic with dress boots, plus its recraftable.
  • It has speed hooks which make the lacing process much faster.
What I Don’t Like
  • I wish these had a leather sole, or at least an option for a leather sole. While the rubber sole offers better traction and comfort (i.e. is pretty much better in every way), leather soles are classic.
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If you want the elegance and sophistication of an Oxford shoe, but in boot form, the Beckett Simonon Elliot is the way to go. It’s my go-to for any fancy situation.

While there are five different leather color options to choose from, I’d opt for either the Brown, Bordeaux (what I have), or Black. Those are the classiest options and best in a dress-formal situation.

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The Beckett Simonon Elliot is my top pick for best dress boot: between the leather, the shape, and the comfort, this boot is hard to beat.

I love the Elliot for many of the same reasons I love the Bolton Chelsea. The Elliot is a unique boot—technically a balmoral boot, the Elliot has the construction of an Oxford dress shoe, but with a full shaft for ankle support.

I wore these to the last wedding I went to and absolutely crushed it on the dance floor as you can see in the pictures above.

While you might want to keep it more classy than me, I can assure you that the Elliot will earn compliments and the elegant styling will help you keep your dignity, even if your best dance move is running around in a circle on the floor.

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There aren’t many reviews for the Elliot specifically, but like I said, many reviewers picked up a second pair of Beckett Simonon boots within the hour they opened their first package. I’d bet the leather will blow you away immediately.

Read My Full Review of the Beckett Simonon Elliot Watch my review of two Beckett Simonon dress boots (including the Elliot) below:
Most Durable
nicks americana flat lay
Nicks Americana
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Price $649
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Boot Type Service
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Suited For Casual
What I Like
  • The upper leather is at least 3mm thick, with the toe cap and heel adding even more leather.
  • The insole and midsole are entirely made with natural materials: thick, sturdy leather.
  • The toplift (or rubber heel cap) is an inch thick, which means it’ll last several years before that part needs to be replaced (which is relatively cheap and easy).
What I Don’t Like
  • The break in is rough.
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If you think you know tough boots, but you’ve never worn a boot from one of the Pacific Northwest boot companies (JK, Nicks, Whites, Wesco), you’re just kidding yourself.

For durability’s sake, I like Nicks Handmade Boots the most. The Americana isn’t their toughest boot, but it blends durability with style the best in my opinion.

I’ve been wearing mine for several months and the leather is still barely even bending.

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I’ll be honest: these are painful to wear new out of the box. But once you break them in, they’re practically indestructible.

Nicks Handmade Boots are mostly made for the wildland firefighters in the Pacific Northwest, so they’re designed to be worn while trekking, chainsawing trees, and literally battling massive fires.

They’re seriously tough. The toughest boots you can get.

The Americana isn’t Nick’s most durable boot, but it’s one of the more “style-forward” options. Their wildland firefighting boots are technically more durable than the Americana, but I’m guessing you’re looking for a casual boot.

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Nicks Handmade Boots have a devoted following because they don’t cut any corners. Every single piece of material used in a Nicks boot is chosen for its ability to take an absolute beating. You can think of them like the Rolex of boots, if a Rolex was built like a tank.

Best Chelsea
Beckett Simonon Bolton Chelsea Boot style on foot
Beckett Simonon Bolton
Get 15% off with code Spy15 Buy Now at Beckett Simonon
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Price $259
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Boot Type Chelsea
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Suited For Smart Casual, Formal, Business Casual
What I Like
  • Beckett Simonon leather is the best at their price point.
  • Blake stitch construction is a classic dress boot method that’s slim and stylish.
  • They’re comfortable and easy to wear all day in an office or at an event.
What I Don’t Like
  • Because they’re crafted to order, your boots may take 6-8 weeks to arrive.
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If you’re patient and can wait the 6-8 weeks for a new pair of boots, I think you’ll be shocked at just how soft and luxurious the leather feels.

The Beckett Simonon Bolton earns my top pick for Chelsea boots because its style is more refined and classic than trendy: it’s a boot that makes you look rich without having to spend more than $300.

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Beckett Simonon is one of my favorite brands, and I usually look to them first for dressier styles because of their leather. The brand was founded by two leather specialists, and that’s really what sets this brand apart: I haven’t found another brand that offers this quality of leather for the price.

They’re very reasonably priced (usually around $220-260), but the quality is more comparable to the $350-$450 boots I own.

There’s one downside, though: getting your new boots can take anywhere between 6-8 weeks because they craft your boots to order. It’s a huge reason they’re able to keep costs low.

The Bolton wins my pick as the best Chelsea boot because it has a classic and refined European shape to it that doesn’t look so trendy. Plus it’s comfortable, and the leather quality sets the Bolton apart.

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You’d be surprised how many reviewers report going back and buying a second or third pair of Beckett Simonon boots immediately after opening their first pair.

And compared to other boot brands with a wait time, Beckett Simonon does a solid job keeping in contact and updating you on your boots while you wait for them to arrive.

See where the Bolton lands when I rank my 13 Chelsea boots from worst to best below:
Best Chukka
Thursday Scout mocha leather detail
Thursday Scout
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Price $160
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Boot Type Chukka
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Suited For Casual, Smart Casual
What I Like
  • It has more shape and style than most other chukkas on the market.
  • The rubber studded sole makes this much more durable than other chukkas, plus it offers more support through the arch because of the steel shank.
  • Like many chukkas, the Scout has two eyelets, and I think three eyelets would be better for more ankle support.
What I Don’t Like
  • Like many chukkas, the Scout has two eyelets, and I think three eyelets would be better for more ankle support.
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I like a chukka that can transition between classy and casual situations. Most chukkas just don’t cut it.

But the Thursday Scout has what it takes. To me, it’s the best chukka boot because it offers arch support, has a durable sole, there are some really cool leather options, it looks stylish, and it’s well under $200. It’s a no-brainer in my opinion. Especially if your only experience with chukkas has been the Clarks Desert Boot.

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I have to be up front here: I’m not a huge fan of chukka boots in general. And I’ve tried dozens.

The only chukka I actually wear with any regularity is the Thursday Boot Company Scout. Why is that?

Well, the Thursday Scout has a leather stacked heel, and the leather upper has contour through the waist of the foot and through the toe. It’s versatile, and it doesn’t end up looking like a leather slipper like so many other chukkas do over time (looking at you, Clarks Desert Boot).

While many chukkas come with a crepe sole, which gets dirty quickly, the Thursday Scout has a custom rubber studded sole that looks classy and lasts much longer. When I wear a chukka, it’s pretty much always the Thursday Scout.

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Because the Scout fits a little looser (due to the two eyelets and general chukka construction), you may want to order a full size lower than your standard sneaker size. I have a full guide to sizing Thursday Boots here.

Best Moc Toe
Red Wing Moc Toe boots
Red Wing Classic Moc
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Price From $299.99
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Boot Type Moc Toe
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Suited For Casual, Work
What I Like
  • The leather options from Red Wing are unique, rugged, and age beautifully.
  • The full grain leather and tightly textured cork in the midsole are durable and break in to feel like a custom fit.
  • It’s made in the USA.
What I Don’t Like
  • I wish the Moc Toe had speed hooks like on the Iron Ranger.
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The Red Wing Classic Moc is the original moc toe, and it’s been extremely popular since the 1950s for a reason.

I have mine in Slate Muleskinner leather, which I love, but the Oro Legacy leather is more iconic and ages so well.

If you work on your feet a lot and you’ve ever struggled with back or knee pain, the wedge soles should help you a lot as they offer more consistent support throughout your entire foot.

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The Classic Moc is a legend, an icon. And for good reason.

This boot made the style popular and has been a staple in workwear for nearly 70 years. There’s been a resurgence of more traditional bootmaking throughout the world in the past twenty years, but for a while, Red Wing was one of the only brands holding it down with all natural materials in the insole and midsole of their boots.

The Classic Moc Toe is tough. Each leather option can handle a beating, but also cleans up well should you decide to wear your moc toe boots in a hang-out situation.

Made with a wedge sole, these offer a lot of grip on concrete and can help a ton if you’ve struggled with knee or back pain in the past.

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From blue collar workers to fashion enthusiasts, the Red Wing Classic Moc Toe is popular with a huge range of people. Getting the right size can be a bit tricky, so make sure you read up on how to find the correct size Red Wings, as they’re not all built the same.

Best Work Boot
model putting on camel city mill lightweight work sock with thorogood moc toe work boot
Thorogood Steel Toe Moc Toe
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Price $254.00
2024-05-05 21:09:05
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Boot Type Moc Toe
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Suited For Work, Casual
What I Like
  • Also available in soft toe, six inch, and eight inch versions.
  • It’s a low maintenance boot, even if you work in rugged conditions.
  • The sole offers the best slip resistance compared to other brands like Danner and Red Wing.
What I Don’t Like
  • The fit is a touch narrow at the ball of my foot—could be just my sizing though.
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For work boots, I’m of the opinion that you want something that’s tough and durable, offers protection, but isn’t so expensive that you avoid actually working in it.

That’s where the Thorogood Moc Toe comes in (especially with the steel toe).

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Some jobs tear through new boots in months, not years. I’m talking about construction, plumbing, electrical: the tough jobs.

Of all the work boots I’ve tested, the Thorogood Steel Toe Moc Toe wins my vote as the best, and it might be for a reason you wouldn’t expect.

First, I like wedge soles for most working conditions. They have a lot of contact with the ground, and the arch support is often critical for guys who experience knee or back pain.

Thorogood is a sturdy boot with good quality leather—where they get me is the price.

It’s a tough boot, it’s comfortable, and it’s not so expensive that you can’t invest in a new pair every year if you need to.

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Most reviewers leave comments like war stories discussing how tough these boots are. The common complaints I see scattered around are that the fit is a bit narrow at the front of the boot. It’s certainly more narrow than the Red Wing Classic Moc, so if you have wide feet, order a size EE or check out the Red Wing.

Read My Full Review of the Thorogood Moc Toe (Non-Steel Version) Watch how the Thorogood Moc Toe stacks up against the Red Wing Classic Moc, Danner Bull Run, and the Thursday Diplomat below:
Best for Winter
moc toe Grant Stone Brass boot black
Grant Stone Brass
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Price $380
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Boot Type Service
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Suited For Casual, Smart Casual, Winter
What I Like
  • I love the style of the Brass boot: it’s a rugged moc toe, but stays fairly slim through the toe.
  • The heavy rubber lug soles give this boot a unique look and also have excellent performance in snow and on icy streets.
  • Horween Chromexcel leather is rugged and durable and can handle being soaked and dried many times over.
What I Don’t Like
  • It’s a heavy boot—one of the heaviest I own. I like that in slippery conditions, but it can be burdensome for some folks.
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The Grant Stone Brass is my personal favorite boot to wear in winter. I do have to make this disclaimer though: I live in North Carolina and it never gets really cold.

With a pair of thick Merino wool socks, the Brass offers plenty of cold-weather protection because of its 3.5mm of leather throughout the upper (when combined with the lining).

If you’re in need of a boot that can handle sub-zero temperatures, then you’ll need an insulated boot. But unless you’re living in a northern state, then the Grant Stone Brass is a stylish and rugged option for those chilly months.

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There are two kinds of boots: winter boots, and boots you wear in winter. If you’re looking for a true winter boot that can take sub-zero temperatures—like something you’d wear on a snow-mobile, then my recommendation here isn’t going to be the best choice.

But if you’re looking for an amazing boot that performs well when the temperature is below freezing, but not below zero, then I recommend the Grant Stone Brass boot.

It’s a moc toe style boot with a 2.5mm Horween Chromexcel leather upper and a 1mm vegetable-tanned natural leather lining. What does all that mean?

You’re getting a thick hunk of superb quality leather protecting you from the elements.

Plus, with the Brass, you get a heavy rubber lug sole that can dig into snow and ice and give you plenty of traction on frozen mud or icy sidewalks.

Because there’s no insulation in the Grant Stone Brass, I recommend wearing a thicker pair of Merino wool socks if the temperature is below freezing. Otherwise, the thick leather will give you plenty of natural insulation on its own.

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When searching through Grant Stone reviews, I’ve found that reviewers are typically on their second or third boot from the brand: Grant Stone gets a lot of repeat customers. And that’s a great sign.

The Brass tends to fit a little larger because it’s built on Grant Stone’s Floyd last. It’s longer, so if you have a more narrow foot, you can order up to a full size smaller than your usual sneaker size.

Best Pull-On Work Boot
Ariat Boots Review Workhog and Midtown Rambler
Ariat Workhog
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Price $214.95
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Boot Type Pull-On Work Boot
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Suited For Work
What I Like
  • They’re heavy-duty, but still lightweight: a nylon shank offers arch support but doesn’t add the weight a steel shank would.
  • These feature a waterproof membrane, so you can stand in water without getting your socks wet.
  • They feature a breathable lining so they’re also a great choice for hot-weather work.
What I Don’t Like
  • The cemented sole construction isn’t the greatest—I’d prefer a Goodyear welt for extra sole stability. That said, this does keep the cost down.
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The Ariat WorkHog isn’t the most durable boot, but if your work is the kind of labor that tends to destroy a pair of boots, you’ll get good use from the WorkHog.

It’s waterproof, lightweight, breathable, and easy to slip on and off. And even better, the price is much more budget friendly than other boot brands.

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The Ariat WorkHog is an awesome waterproof pull-on work boot. It’s western-style, but built with a ton of modern materials and features.

I chose this boot as my top pull-on work boot because it’s so comfortable. Ariat uses their ATS insole system, which is basically like stepping on a memory foam mattress.

These boots are also relatively easy to slip on and off, which isn’t always the case for western-style boots (notoriously difficult to pull off). This is great if you have a stiff lower back and need to keep your bending to a minimum.

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The Ariat WorkHog has a loyal fanbase of blue collar workers who seem to get a new pair every year. That’s an important thing to note on this boot: it’s not built to last forever.

It’s a great choice if your work is really tough and you tend to absolutely destroy boots within a year.

Read My Full Review of the Ariat Workhog Find out what the WorkHog looks like cut in half in my video below:
Most Comfortable
close up Red Wing Classic Chelsea toe
Red Wing Classic Chelsea
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Price $299.99
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Boot Type Chelsea
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Suited For Casual, Work
What I Like
  • The leather Red Wing uses from the S.B Tanning Company (Red Wing owned) is phenomenal. I have the Ebony Harness leather and it ages so well.
  • Because it’s a Chelsea, it slips on and off easily: another bonus for guys with stiff backs.
  • It’s a durable boot and an excellent choice for working applications.
What I Don’t Like
  • I think it’s ugly. I like the bump toe last (same as on the Iron Ranger), but I just don’t think wedge soles look good. Obviously, this is completely subjective.
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If you’re looking for a comfortable boot, get a pair of Uggs. If you’re looking for a comfortable boot you can work in and that will last several years, get a pair of the Red Wing Classic Chelsea.

I’m not crazy about how the wedge sole looks, but I know plenty of guys who love the style. But style aside, the wedge sole can be a game-changer if you struggle with low-back pain or knee pain. Because the sole is in complete contact with the ground, your arch gets more support, which can help with your posture.

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The Red Wing Classic Chelsea wins my vote for the most comfortable boot for a few reasons (one which you might not expect).

First, it has a leather midsole which is awesome for durability, but the insole is made with high-grade Poron. This is unusual for Red Wing, as they normally use all-natural materials. But Poron isn’t a bad thing: it’s way more comfortable and easier to break in than leather.

And the Classic Chelsea has a wedge sole. If you struggle with low back pain or knee pain, you should definitely try a wedge sole. Many people I know who have pain from previous injuries (or a lot of bending) love wedge sole boots and swear by them.

Wedge soles have a lot of support through the arch (they’re in contact with the ground throughout the entire boot).

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When Red Wing first released this boot, Red Wing fans were very upset because it has a Poron insole rather than leather. But more and more reviews have been pouring in discussing how comfortable they are. And just because they’re comfy doesn’t mean they’re not tough little beasts.

Best Cowboy
jeans over Tecovas Cartwright boot shaft
Tecovas Cartwright
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Price $275
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Boot Type Cowboy
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Suited For Casual , Smart Casual
What I Like
  • Tecovas uses traditional boot-making methods like driving in lemonwood pegs into the arch area.
  • The leather stacked heel gives a great feeling of authority with every step.
  • The upper leather is buttery smooth and there’s no break in.
What I Don’t Like
  • There aren’t many leather options available.
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A great pair of cowboy boots usually costs a small fortune. Sure, there are more nuanced and fancy cowboy boots on the market, but if you’re looking for a fantastic value cowboy boot that looks as good on the ranch as it does in the office, then the Tecovas Cartwright is the boot for you.

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A good pair of cowboy boots can make a man stand taller. Of course, I mean that literally, but also in the figurative sense.

The longer I’ve been in the boot-world, the more I’ve come to appreciate a fine pair of western-style boots.

And for my money, I like the Tecovas Cartwright the most.

Tecovas builds their cowboy boots in Leon, Mexico, which is the cowboy boot capital of the world. The leather they use is soft and buttery, and there’s plenty of support through the arch.

The Cartwright is built in the traditional way: lemonwood pegs through the arch, steel shank, leather stacked heel, and leather sole. It’s a beautiful boot, and it’s an excellent value for the price.

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Reading through the reviews online, some folks felt the Cartwright fits a little large (though the majority agree they’re true to size). I picked up my Tecovas Cartwrights in my sneaker size and feel the fit is perfect. Whenever I wear my cowboy boots, I tend to wear them all day, and when my feet start swelling, I like the bit of extra room.

Best Under $100
New Republic Sonoma front view on foot
New Republic Sonoma
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Price $99
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Boot Type Chelsea
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Suited For Casual, Smart Casual
What I Like
  • The suede is nice—it’s not mind-blowing, but it’s decent, especially for the price.
  • They’re comfortable due to the high density foam insoles and the crepe rubber sole.
  • New Republic offers a few different suede color options which are all stylish.
What I Don’t Like
  • Crepe rubber soles can get dirty quickly, which is the main reason I’d never get the Common Projects, but is also a drawback here.
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There aren’t many boots worth getting below $100. In fact, the New Republic Sonoma is the only boot I recommend that costs under a bill, and there’s a big reason for it: I think it’s a way better alternative to the super expensive Common Projects Chelsea.

The Sonoma and Common Projects both feature a crepe sole, which is going to look very dirty in a month or two of wear. So you might as well save $400 and get the New Republic.

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There aren’t many good boots under $100, and if you’re looking for a truly budget boot, then you’re not going to have a ton of rugged, durable options.

But there is a gem hiding in the bargain basement: the New Republic Sonoma. It’s a light sandy suede Chelsea boot, and it’s pretty solid.

Obviously, it’s a certain style, and you have to be down with that. But considering that a pair of very similar looking Common Projects Chelsea boots sell for $500+, and you can get the New Republic instead, which is nearly identical, for under $100, I think it’s a winner.

What Other Reviewers Say chevron-down Created with Sketch Beta.

Many reviewers naturally compare these to the Common Projects Chelsea, which makes sense because the New Republic Sonoma is what one might generously call an homage to the CPs.

The Sonoma doesn’t last as long as Common Projects—many reviews I read give the Sonoma about 24 months of life, whereas many Common Projects wearers get about double that. But the New Republic Sonoma also costs about a fifth of the amount of a CP Chelsea.

Read My Full Review of the New Republic Sonoma Watch below to learn why I think the New Republic Sonoma is better than the $500+ Common Projects

My Advice on Building a Versatile Three Boot Collection

Maybe a bit cheeky, but I think every man should own at least 3 pairs of boots. Of course, in the video above, I couldn’t just stop at 3 boots…I had to pick 5.

1. A Brown Service Boot

Grant Stone Diesel 2
The Grant Stone Diesel

A simple brown service boot is the most versatile boot any guy can have. It goes with everything.

Depending on your price range, some good examples are:

2. A Classy Dress Boot

Beckett Simonon Elliot close up bordeaux leather
The Beckett Simonon Elliot

Whether it’s for going into an office, going to a wedding, or other more formal events, it’s important to have a great pair of dress boots. You might not wear them all the time, but owning a pair will certainly come in handy for special occasions.

Some good examples are:

3. A Durable Work Boot

JK OT Boots in redwood roughout leather
The JK O.T.

Even if you don’t work a job that’s tough on your boots, having a durable pair of work boots is a must for every man. For me, I want a boot I’m confident can last 10 years or more.

Earlier, I recommended the Thorogood Moc Toe as the best work boot. That’s a great option. My personal go-to now is the JK O.T. ($549).

This 60-second video explains how you can tell if a boot is high quality or not when you’re shopping.

What Do Other Boot Experts Say?

While I’ve reviewed over 100 pairs of boots, sometimes it’s good to hear others’ opinions. So I researched what three other experts in the boot-world say their favorite boots are.


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Nick at Stridewise has also reviewed over 100 pairs of boots. Maybe more at this point. His top recommended boot is the Thursday Captain.

As a runner up (as a higher quality and higher priced pick), Stridewise’s #2 boot is the Oak Street Bootmaker’s Trench Boot.

Oak Street Trench Boot

Built with thick 3mm Horween leather, the Oak Street Trench is rugged---even for a service boot.

Check Price Read Our Review

Rose Anvil

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Weston Kay, the founder of the Rose Anvil YouTube channel (aka the guy you’ve seen cutting boots in half) also released his list of the best boots a guy can get.

His most recommended boot is the Thorogood Moc Toe.

And Rose Anvil’s pick for the best value boot on the market is the JK 300.

I went and visited JK Boots in Washington, and I can confirm that they make incredible boots (all handmade, too).

I was very impressed with JK Boots when I visited their factory.


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Fjorde is a force in the heritage style world, and while he doesn’t specifically review footwear (denim is his specialty), he’s had experience with some of the highest-end boot brands in the world.

For him, it’s not so much the brands that are important, but the styles. His two most recommended types of boots are:

  • Combat, or service boots (like the Grant Stone Diesel)
  • Engineer boots (like the Wesco Mr. Lou)


Thursday Scout mocha weathersafe suede burnishing leather detail
Walking in my Thursday Scout

As you can tell, I’ve bought and worn a ton of boots. 

What I’ve learned is this: you usually get what you pay for, and there are a few brands out there that offer exceptional value for your money. 

There are still some brands out there I haven’t tried. But I’ve bought and worn boots from nearly all the big-name brands.

This list is made with love and with years of research. And not just my own experience, but also the experience of the tens of thousands of readers and viewers in the BootSpy community.

Come nerd out with us on the BootSpy YouTube channel or on Instagram. And please leave a comment below letting me know what your favorite boot is.


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  1. Stan Adams

    Hey, William ~

    I really need some guidance to find the boot that I have been searching for: a black engineer style boot for riding my motorcycle. I used to have a decent one from Red Wing, but it died, and they have since stopped making that style.

    What are your recommendations?

    Thank you…And I am glad that I came upon this FB page today.

  2. Doug Emory

    Great information