7 Best Chukka Boots for Men: The King of Ankle Boots

This post contains affiliate links. If you click on a link and make a purchase, we may earn a commission at no additional cost to you. Learn more.

by  William Barton | Last Updated: 

If you’re going to buy a new pair of boots, you want to get every bit of value you can, right? Nobody wants to drop top dollar on a mass-produced pair of doo-doo boots.

I’ve done all the research and tested all of these brands myself, and I can confidently say these are the best chukka boots for men on the market right now.

Best Value
  • Classic stitchdown construction
  • Shock absorbent and comfortable rubber studded outsole
  • Available in WeatherSafe suede and full grain leathers
Best Dress
  • Incredible Italian full grain leather
  • Leather sole for more formal look
  • Recraftable and refined Blake stitch construction
Best Desert Boots
  • Desert boot style with premium materials
  • Available with smooth suede calf leather and full grain calf leather
  • Natural leather lining
Best Suede
  • Thick crepe rubber sole and C.F. Stead suede leather
  • Goodyear welt construction for recraftability
  • Full vegetable tanned leather lining, midsole, and insole for longevity
Best Waterproof
  • Horween leather upper with waterproof lining throughout the boot
  • Rubber lug sole for added traction in wet conditions
  • Leather stacked heel and broguing detail on the back
Best for Wide Feet
  • Available in EE wide sizes
  • Full grain Italian leather with cork filler and a steel shank
  • Made in the same workshop as Ferragamo and Louis Vuitton
Best American Made
  • 100% handcrafted in the United States
  • Horween Orion suede leather plus Dainite rubber stud sole
  • Recraftable, so it can last decades

Chukka boots are tricky: with such a simple construction, a low-quality pair quickly stretches out and looks too floppy. 

So it’s important to get a chukka that’s been tested. But that doesn’t mean you need to drop a ton of money to get a solid pair of chukkas. 

Chukkas are one of the few boots you can wear year-round—when the weather gets hot, they’re not punishing, and they’re an excellent choice for the office. 

I’ve tried dozens of these boots over the years, and I’m confident in saying that these are the best chukka boots for men on the market right now. 

How Did I Come Up With My List?

model wearing Thursday Scout
Wearing my Thursday Scout chukkas

This list comes from a combination of hundreds of hours of research over the years, plus testing dozens of boot brands. 

I’ve recrafted boots, I’ve bought some clunkers, and I’ve honed in on a few brands that consistently make a great product. 

I don’t own all of these boots, but I do own at least one pair of boots from each brand (I own multiple pairs from four of the brands on this list). This isn’t just a roundup of different boots I randomly found—this is a list of chukkas from brands that offer the best value-for-money you can find. 

Whether you want a dressy chukka for more formal events, or you want something comfortable and casual, I’ve broken it down into categories so you can find the perfect chukka for you. 

7 Best Men’s Chukka Boots Around Right Now

Best Value: Thursday Boot Company Scout

Thursday Scout profile view

The Thursday Scout is my personal favorite chukka. It wins out for me because its shape and style make it a versatile option, whether you want to wear it casually or more formally. 

If you do want a chukka for a more formal event, choose one of the full grain leather options rather than the suede (suede is more casual, and Thursday’s WeatherSafe suede has burnishing on the toe and heel, which make it definitively casual). 

Most chukkas are made with a stitchdown construction, and the Scout is no different. The poron insole makes for a very comfortable experience right out of the box, and I love that the Scout has a classy leather stacked heel.

What I Like

  • The Scout is traditionally crafted, but has modern sole materials that make it comfortable and durable. 

  • There’s a wide variety of leather options available, from casual WeatherSafe suede to more dressy full grain leathers. 

  • The style is slimmer than most other chukkas, plus the leather stacked heel give the boot a more classy, refined look.

What I Don’t Like

  •  With two eyelets, there’s not a lot of ankle support—though that’s common with all chukkas. If you need ankle support, I recommend a different style of boot altogether.

What Other Reviewers Say

At the time of writing, the Thursday Boot Company Scout has over 3,000 reviews with a 4.8-star average rating. 

Many reviews claim these are the most stylish chukkas they’ve seen, and many of the negative reviews are focused on the narrow fit. These two issues go hand-in-hand: if you have a wider foot, I recommend ordering one of the EE/EEE Wide sizes. 

You can read my in-depth review of the Thursday Scout here.

The Verdict

The Thursday Scout is my go-to chukka boot and my top recommendation. 

There’s a wide variety of leather and sizing options, so I’m sure you’ll be able to find a leather that suits your needs. 

The style of the Scout reminds me of more expensive brands, but the cost is well under $200, making this boot a total bargain.

Best Value for Money
Thursday Scout

The Thursday Scout is one of the best bang-for-buck chukkas on the market. With Thursday's proprietary leather and a stitchdown construction, this boot is hard to beat for value.

Check Best Price Read Our Review
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Best Dress: Beckett Simonon Ellis

View this post on Instagram

Beckett Simonon is one of my top three favorite brands and it’s because their boots have incredible leather quality you can’t find elsewhere in footwear that cost less than $300. 

Shopping with Beckett Simonon is a bit different, though. They make their boots to order, so you may have to wait 8-12 weeks to actually get your Ellis chukkas.

In my opinion, they’re absolutely worth the wait—made with classic Blake stitch construction, incredible leather, and a stylish silhouette, the Ellis is easily the best dress chukka for the money, in my opinion.

What I Like

  • The full grain vegetable tanned Italian calfskin leather is phenomenal, especially considering the price of the boot. 

  • They’re comfortable and are fully leather lined. The leather sole also makes it a good option for formal-wear.

  • The shape and style is sophisticated—I’d compare these with $400-$500 chukkas.

What I Don’t Like

  • There are no wide sizes available.

  • Because they’re made to order, it can take several weeks or even months to get. 

What Other Reviewers Say

The words “quality” and “craftsmanship” pop up in a lot of reviews for the Ellis. Typically, people who buy one pair of Beckett Simonon boots end up getting a second and third pair. But you have to be patient—there are also a few reviews from folks who felt the wait-time was too long.

The Verdict

If you’re patient and can wait several weeks (or months), the Beckett Simonon Ellis is one of the best “bang-for-your-buck” chukkas you can get.

With Beckett Simonon, it’s all about the leather. The Italian full grain calfskin leather is so soft and buttery-smooth: these boots easily look double the price.

Best Dress Chukka
Beckett Simonon Ellis
(Get 15% OFF with code Spy15)

The Ellis is my favorite dress chukka because it’s simple, clean, and the leather is absolutely phenomenal.

Check Best Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Best Desert Boots: Velasca Umbrelee

View this post on Instagram

Not all desert boots are created equal. 

Of course, there’s the original, the icon, the classic: the Clarks Desert Boot

But other brands have swooped in and improved on the details and design. My favorite desert boot is the Velasca Umbrelee. The big differentiator between Velasca and Clarks is the material quality, which makes a huge difference in the longevity of the boot.

Compared against one another, your Velasca’s will retain their shape a lot longer. Plus the crepe sole won’t wear away, and the paint along the side of the crepe sole will keep them looking classy for longer, too (white crepe turns gray and nasty looking quickly).

What I Like

  • The crepe rubber used for the sole makes for a very comfortable boot, but it’s also more durable than other crepe rubber soles.

  • The suede leathers all have a fine knap texture that’s visually pleasing. 

What I Don’t Like

  • Only suede versions are available—no full grain leather options. 

What Other Reviewers Say

Customer service is a big win for Velasca. Their communication and quick exchanges are frequently mentioned in reviews. 

A few reviewers had a tough time getting the correct sizing as Velasca uses European sizing standards rather than US standards.

The Verdict

If you want a desert boot that’s still going to look good six months after you buy it, I recommend the Velasca Umbrelee. Most of the big improvements over the reigning champion, Clarks, are with the crepe rubber sole. But with desert boots, it’s pretty much all about how the crepe sole holds up. 

Best Desert Boot
Velasca Umbrelee

With a painted crepe sole and a refined shape, the Velasca Umbrelee is the grown-up version of the iconic desert boot.

Check Best Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Best Suede: Grant Stone Chukka

View this post on Instagram

Grant Stone is another one of my favorite brands because they consistently focus on making the best boots inside and out. 

Most brands (including a few I love) skimp on the insides of their boots—they’ll use fiberboard instead of leather, synthetic insoles instead of natural, use fabric in the lining, etc. But Grant Stone never pulls its punches on quality and durability. 

With a 3mm piece of vegetable tanned leather for the insole, these boots should last you a decade with any sort of regular care. Plus the suede is a C.F. Stead calfskin leather, which will also stand the test of time. 

Like many chukkas, the Grant Stone Chukka features a crepe sole, but it has the addition of a steel shank, which helps a lot with arch support.

What I Like

  • This chukka uses calfskin suede from the C.F. Stead Tannery, which is super nice. 

  • The vegetable tanned leather insole, midsole, and welt all make for a very durable boot.

  • The crepe sole has a lot of cushion and shock absorption, and the steel shank adds arch support back into the sole—the best of both worlds. 

What I Don’t Like

  • While it represents amazing quality, the Goodyear welt looks a little bulky on this design.

What Other Reviewers Say

Because chukkas have a very simple construction, they can often look a bit flimsy. For folks who feel that way, but are still eager to embrace a chukka’s casual style, the Grant Stone Chukka is a winner. Several reviewers mention the sturdy look and feel of these boots.

The Verdict

In terms of build quality and construction, the Grant Stone Chukka is the best boot on this list. The Goodyear welted design adds a bit of bulk to this boot, so it’s not quite as elegant as the Beckett Simonon or Thursday chukkas, but this boot should last well over five years of regular wear. 

Best Suede Chukka
Grant Stone Chukka

With a 3mm piece of vegetable tanned leather for the insole, these boots should last you a decade with any sort of regular care. Plus the suede is a C.F. Stead calfskin leather, which will also stand the test of time. 

Check Best Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Best Waterproof: Allen Edmonds Venture

View this post on Instagram

Allen Edmonds is an iconic American brand, and they’re one of the few great boot brands that also offer fully waterproof heritage styles. 

The Venture chukka is built for bad weather—with it’s lugged rubber outsole and waxed weatherproof Horween leather, the Venture is an excellent choice if you walk as part of your commute and get caught in the rain often. 

What I Like

  • The waxed Horween leather is very high quality considering the utilitarian use-case for these boots. 

  • The rubber lug sole offers a lot of traction on wet cement. 

  • It’s one of the few good looking waterproof chukkas—most others look cheap.

What I Don’t Like

  • There aren’t a lot of leather and size options. 

What Other Reviewers Say

Some reviewers felt that adding a fourth eyelet would make more sense given that this is a chukka you’d expect to wear in the rain. Personally, that’s the main reason why I’d get a six-inch boot, or something other than a chukka for inclement weather. But if you’re committed to chukkas, even in the rain, this is the one for you.

The Verdict

Allen Edmonds has been making high quality boots and shoes for 100 years, so they’re doing it right. The Venture chukka is one of the few truly waterproof chukkas that are built well and look stylish. While I’d like to see more leather options, what they do have available is quality through and through.

Best Waterproof Chukka
Allen Edmonds Venture Weatherproof Chukka

With it’s lugged rubber outsole and waxed weatherproof Horween leather, the Venture is built for bad weather.

Check Best Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Best for Wide Feet: Idrese Hudson

View this post on Instagram

Idrese is a lesser-known brand, but they custom-make their boots and shoes to order and the quality is outstanding. 

You can even design your own boots with unique leathers, various soles, and interesting features you can’t find on other boots. 

The Idrese Hudson is an excellent blend between dressy and casual: with a rubber studded sole, you get plenty of traction, and the upper has an elegant shape that’s fit for the boardroom. 

Available in EE wide sizes, the Hudson is an excellent chukka for guys with wider feet. 

What I Like

  • There are EE widths for a huge variety of sizes and half-sizes.

  • Two simple classic suede options, and two full grain leather options. 

  • They’re made in the same workshop as Ferragamo and Louis Vuitton.

What I Don’t Like

  • Because these are handmade to order, they can take up to (but usually not longer) than four weeks to get to you. 

What Other Reviewers Say

There aren’t a ton of reviews for Idrese online—they’re still a growing and relatively small brand, but I’ve custom-made a pair of Chelsea boots from them and I can vouch for the quality.

The Verdict

Having wide feet often means wearing ill-fitting shoes. Of course, if you can find a pair of boots in EE or EEE widths, then it’s no issue. But chukkas rarely come in wide widths. 

The Idrese Hudson solves that problem in style.

Best Chukka for Wide Feet
Idrese Hudson

Hand crafted to order, the Idrese Hudson has a EE width available, making it a fantastic option for guys with wider feet.

Check Best Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Best American Made: Oak Street Bootmakers Campus Chukka

View this post on Instagram

Oak Street Bootmakers are USA-made all the way through. They even source their eyelets and steel shanks from the USA. That’s pretty incredible.

This chukka made my list of the best American made boots because it represents some of the best quality boot making in the States. 

With a 360-degree Goodyear welt and a Dainite studded sole, Oak Street only uses the best quality materials in this chukka.

What I Like

  • The shape is unique and stylish, even among chukka boots. 

  • Everything in this boot (besides the English Dainite sole) is sourced and manufactured in the USA.

What I Don’t Like

  • There are few color and leather options. 

What Other Reviewers Say

Oak Street is another relatively unknown brand, but die-hard boot enthusiasts absolutely love them. Few other bootmakers go as in-depth as Oak Street in quality craftsmanship and manufacturing, and that’s true across their entire line of boots.

The Verdict

If quality and American craftsmanship are your top two priorities, then the Oak Street Campus Chukka is the boot for you.

Best American Made Chukka
Oak Street Bootmakers Campus Chukka

If a USA-built chukka is what you’re after, the best of the best is from Oak Street Bootmakers. Their Campus Chukka is made with Horween leather, a solid Dainite sole, and a weather resistant 360-degree Goodyear welt (a Barbour welt, no less).

Check Best Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

What are Chukkas?

model walking down stairs wearing clarks leather desert boot chukka
Clarks Desert Boot

Chukka boots are lace-up ankle boots. Most chukkas are made with full grain leather or suede, but there are canvas and wool chukkas around (but they’re far less common). 

I categorize chukkas in three ways: dressy chukkas, casual chukkas, and desert boots. Desert boots are the least formal because of their crepe sole and relaxed shape. They can also be the most comfortable, especially if you’re standing on your feet all day. 

model wearing Thursday Boots Scout chukka in mocha
Thursday Scout

Chukka boots got their unique name likely from their use in the game of polo. Officers in the British Colonial Army and polo players often wore these types of boots when not playing or when off-duty because they were so comfortable in comparison to the knee-high boots worn during the time. 

Chukkas are a fantastic year-round boot. Because they’re shorter in the ankle (typically around four inches rather than six), they offer more airflow and breathability compared to most other boots. That makes them one of the few boot styles that stay comfortable in the hotter months. 

Of course, chukka boots work well in colder months, too—especially suede pairs in fall. That style is unbeatable. 

The style is defined by its open lacing and typically has two or three eyelets. Some versions, like Clarks, can be slipped on and off, but more formal versions need to be tied and untied. 

Clarks Desert Boot

The highlight of the Clarks Desert boot is the richly oiled pull up leather and the simplicity of its construction. While the crepe sole is delicate, it provides a lot of cushion, though you’ll need to give these boots a rest every so often.

Check Best Price Read Our Review
If you click this link and make a purchase, we earn a commission at no additional cost to you.

How to Wear Chukka Boots

Author William Barton modeling Thursday Boots Scout chukka in mocha weathersafe suede

Chukka’s are a versatile boot, though the best ways to style them really depend on the type of chukka you get. 

As I mentioned earlier, there are three levels of formality with chukkas: formal, casual, and desert boot (most casual). 

I personally like chukkas with a rubber sole (opposed to crepe) because the color remains the same. Creme colored crepe soles can get dirty quickly and turn gray, making a six-month old boot look ancient. 

View this post on Instagram

Wear your chukkas with jeans and chinos. If you have a formal chukka like the Beckett Simonon Ellis, you can even wear that with a suit (but it still pairs with jeans, too). 

A fantastic outfit is a chukka, pair of jeans, t-shirt, and a bomber jacket on top. It’s super simple, easy, and looks polished. 

You can read our guide on how to style chukka boots here

Chukka, Chukka, Bow-wow

You’re armed with the knowledge to buy the best chukka possible, and to style it like a boss. 

All things considered (price, too), my favorite chukka is the Thursday Scout. It’s versatile, comfortable, stylish, and the price is right. But if I wore more formal clothes—even business casual to the office—I’d choose the Beckett Simonon Ellis.

Thursday Scout

The Thursday Scout is one of the best bang-for-buck chukkas on the market. With Thursday's proprietary leather and a stitchdown construction, this boot is hard to beat for value.

Check Best Price Read Our Review
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Of course, there are plenty of other considerations, like if you’re caught in the rain or if you have wide feet. In any case, you can’t go wrong with any of the chukka boots here. So which one are you getting?

Exclusive Discount Available
Beckett Simonon Ellis
(Get 15% OFF with code Spy15)

The Ellis is my favorite dress chukka because it’s simple, clean, and the leather is absolutely phenomenal.

Check Best Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

FAQs

Are chukka boots popular?

Chukka boots are very popular—they’re one of the most common types of boots around. Because of that, you want to find a chukka that looks distinctive so you’re not blending in with the crowd.

Are chukka boots good for feet?

Chukka style boots don’t offer a lot of ankle support, so that’s important to note before buying. Many chukkas have soft crepe soles, which are excellent for shock absorption and all-day comfort. Just make sure that your boot also has a shank in the arch if it’s a crepe sole because that’ll lend much-needed structure and support.

What are chukka boots good for?

Chukkas are ideal for casual style. They’re easy to put on, and they pair well with jeans, chinos, and formal versions even look fantastic with a suit. 

Shop This Post

If you click these links and make a purchase, we earn a commission at no additional cost to you.