The chukka boot is a simple yet versatile boot that looks good with almost any outfit in any situation. If you don’t have a pair in your collection, you should absolutely consider picking one up.
Chukkas are kind of like the
Every guy needs at least one pair of chukkas in his closet, which is why we’ve created this list of the best chukka boots for men.
Short on time? Here are our top three picks for the best chukka boots you can buy right now:
The Scout is perhaps the best chukka in its price point, and it’s a good choice for budget-minded buyers and chukka connoisseurs alike.
This might be the most popular chukka on the market. Its military heritage and timeless design are why it’s still a bestseller to this day.
This is a casual, rugged (but lightweight) chukka boot that's comfy right out of the box.
Read on for more info and the full list…
The 8 Best Chukka Boots for Men
No matter your budget or style preferences, you’ll find a pair of chukkas on this list that will work for you.
#1: Clarks Desert Boots
We’ll start off with what might be the most popular chukkas out there: the Clarks Desert Boots. Its military heritage and timeless design are why it’s still a bestseller to this day.
Desert boots are a type of chukka introduced by Clarks in 1950 that became popular with army officers, so it’s safe to say these are the best desert boots you can buy. Based on the boots these officers wore in desert environments, desert boots are characterized by their crepe soles and soft suede uppers.
These boots have a casual, rugged appearance, so if your style is the least bit outdoorsy, these boots will fit right into your wardrobe. They’re also nice for a laid-back smart casual look (or just straight up casual looks).
#2: Red Wing Shoes Weekender Chukka
Red Wing Shoes is another footwear heavyweight that makes some excellent chukkas.
Their Weekender Chukkas offer a more structured take on the chukka form as well as a healthy amount of Red Wing’s trademark workwear style.
While the chukka usually has a distinct form, the Weekenders have a more traditional boot appearance. However, the essence of the chukka is still here: the ankle length, open lacing system, and three pairs of eyelets.
Made with a full-grain leather upper, cork midsole, and stitchdown construction, the Weekender is built to last.
Even though it’s called the Weekender, it’s good for everyday wear, and it can even be dressed up a bit. This is a great boot to consider if you want more of a hybrid chukka.
#3: Thursday Boot Co. Scout
Longtime readers of The Modest Man will recognize the Thursday Boots name. Simply put, we love them because they offer fantastic value for the price, and their Scout chukkas are no exception.
Featured here in the ash colorway, the Scout is a classic casual chukka that mixes British and American boot styles. You’re getting handcrafted Goodyear Welt construction, shock-absorbing insoles, and a fully lined glove leather interior, all for the shockingly low price of $149.
The Scout is perhaps the best chukka in its price point, and it’s a good choice for budget-minded buyers and chukka connoisseurs alike. If you put your boots through a lot of wear and tear, check out their Rugged & Resilient line, which uses even more durable materials.
#4: Allen Edmonds Williamsburg Chukka Boot
Men’s leather chukkas usually lean more casual, but that doesn’t mean chukkas can’t be dressy. Exhibit A: these super classy chukkas from Allen Edmonds.
While most chukkas use suede, the Williamsburg uses a smooth European leather that makes these boots look more like dress shoes. Combine that with the squeaky clean two-eyelet lacing system, and you’ve got an elegant chukka that’s also a dress boot.
Featuring handmade Bench Welt construction, a single oak leather sole, and soft leather lining, the Williamsburg is a hardy, reliable boot. Allen Edmonds has a reputation for well-made items, so you know you’re getting a high-quality product here.
These boots are great for semi-formal or business casual atmospheres, but you can also dress them down.
#5: J. Crew MacAlister Boot
The MacAlister chukka from J. Crew has popped up on TMM several times before and for good reason. This simple, casual chukka is a solid choice that’s easy to love.
These relaxed desert boots pair well with casual outfits, and like other chukkas, you can also dress them up quite a bit. Their structured silhouette, sneaker-style cotton laces, and rubber sole help this chukka strike a nice balance of casual and formal.
The anchor grey color is a lovely dusty shade that’s neutral without being boring. No, these aren’t artisanally made boots, but you’re getting a lot of value for the price (especially if you can pick them up on sale).
#6: Shoe the Bear Dalton Chukka
Scandinavian countries are often associated with minimalism, and Denmark-based footwear company Shoe the Bear is an excellent example of that design philosophy as applied to shoes.
Simple without being plain, their Dalton Chukka (Amazon affiliate link) is a sleek, elegant boot. With a structured suede upper and a rubber-coated leather outsole, the Dalton is one of the most timeless-looking chukkas we’ve seen.
While it looks fairly vanilla at first, look close and you’ll see small details, like the gentle flourishes that the stitching provides and the coloring on the heel.
These boots lean a bit more formal, so if you typically wear smart casual or business casual, you’ll get a lot of mileage out of them. The tobacco colorway is shown here, but the Dalton also comes in black and brown.
#7: Ace Marks Lorenzo
Here’s another dressy take on the chukka from Ace Marks, a brand that exploded when it raised over $1 million on Kickstarter. Today, they’re going strong on their own, continuing to offer luxury-level shoes like their Lorenzo chukka.
These are really dressy chukkas, so much so that they could almost be worn in formal situations. The burnished leather, clean eyelet pair, and elegant outline make the Lorenzo a truly sophisticated boot. These are handmade in Italy from high-quality leathers, and blake flex construction is used to ensure durability.
If you dress business casual a lot, these could be the best leather sole chukka boots for you. They’re also a good option if you dress smart casual and want some footwear to elevate your outfit.
#8: Rancourt & Co. Acadia Chukka
Together with L.L Bean, Rancourt & Co. helped to define the New England prep style, and you can see that style on full display with their Acadia chukka boots.
These durable, water-resistant boots have an undeniably northeastern look to them. Made from Horween Chromexcel leather, the Acadia is a long-lasting boot that features Rancourt’s caliber sole, which is a crepe wedge style sole that affords extra durability.
Even though the Acadia might seem strictly casual at first glance, it’s surprisingly classy. Its profile, while a bit chunkier, is still handsome. Even if you don’t dress in a particularly outdoorsy fashion, you can still incorporate the Acadia into many of your casual outfits.
Chukka boots have a lot going for them, and if you don’t have a pair, you owe it to yourself to pick one up. They’re one of the most versatile types of boots, and as you can see, there are tons to choose from.
Which of these are your favorites? Did I miss your favorite pair of chukkas? Let me know in the comments!
Paul G says
The only AUTHENTIC chukka boots and shoes always available are UK made George Cox. They still make the exact ones they’ve been making since way way back when. With the proper crepe sole with the crinkley wrap-around. Plus their rather exciting modern twists too.
The ones above are more “desert” boots with very thin soles, which defeat the whole point of WHY folk wore both creepers and chukkas. Which is for that bouncey comfort and that they are excellent shoes for shuffling or bopping.
Whereas the above are more, despite looking nice, just basic town shoes in a basic desert boots style.
Konstantinos Mandilaris says
I am curious, how do you end up on recommending these brands? It just goes around to show that you are not really a shoe enthusiast. I can list you 20 brands worth it more than those that are better built, have better design, materials and construction. Here are 10.
1) Carlos Santos
3) Meermin (even them yes)
4) TLB Mallorca
6) Vass Budapest
7) Enzo Bonafe
8) Alden (since you like “American Made”)
9) Grant Stone
10) Antonio Meccariello
You seem to be focusing a lot on these “budget” affiliate brands. Of course because it brings revenue. However there is no excuse for a man to not buy a welted shoe in 2020. If your budget is as strict then buy Meermin for 200$ as you can at least resole them.
Sorry if this sounds harsh but every menswear blog I stumble upon rehashes the same thing. Let’s promote Clarks, Ace Marks (🤢) and Thursday (which are ok at least).
Hmm let’s see: Nisolo, Alen Edmonds, Thursday, Rancourt, CDB, Redwing – all welted (Goodyear, hand or stitchdown). Ace Marks is Blake Stitch (can be resoled).
J. Crew Macalister is one of my personal favorite desert boots. They hold up remarkably well for the price and are super comfy.
I’ve never heard of your #1 pick, but I see that you sell them on your site.
Who’s biased again?
Konstantinos Mandilaris says
thank you for replying. Yes, I must admit I am a little biased when it comes to the first brand. But I wouldn’t have quit my engineering job to work with a brand I don’t believe in. It is not an unknown brand if you are a shoe enthusiast.
Also, please don’t get me wrong, I am an avid reader of your site and actually love the content on your fulltimeblog website.
I think our main difference (as in generally we, not particularly you and me) is a potential language barrier (english is not my native tongue) and the different styles in Europe and the USA. I frequent the Goodyear Welted Subreddit often and there is a very very strong interest in bulkier, chunkier and rounder aesthetics there. Please correct me if I am wrong.
For me the word Best should describe Best. I have handled Allen Edmonds (don’t you agree that their quality and QC has gone down the drain since 2013?) Ace Marks, Magnanni, Redwing etc. and I do have actual training in leatherworking and upcoming bespoke shoemaking classes in 2021-2022. I cannot consider a shoe that costs 150$ the best. Maybe the best in it’s price range, sure.
I will however try to defend some of my points. What I really want to say is that there is a very heavy focus of blogs and lists (especially Business Insider and co.) on more US type of brands. Where are the Europeans in this list?
1) Nisolo is a Mexican ethical brand (afaik). For 100$ during sales or $155 or so in retail they are not terrible. I am not familiar with them but some users called them “wearing a cardboard box on my foot”
2) Allen Edmonds are the ones that look the nicest for me on your list and if I lived in the USA I would consider them. However in Europe it is not worth it (import taxes, shipping etc).
3) Rancourt: another USA Brand (which admittedly I don’t know much about) with good reputation on reddit and other forums, especially for their moccasins/boat shoes. Certainly not my style aesthetically but I do appreciate that they are a small business and they have handsewn aprons.
4) Paul Evans and Ace Marks are not worth the full retail price. If you like the aesthetics and the black construction, sure no problem. But I know where Paul Evans makes their shoes and what is their wholesale price so I understand their business model and no they are not 600$ shoes for 300$. You can buy TLB Mallorca for that price and a much much better shoe. That being said, while I am a fan of hand-welted and Goodyear welted shoes there’s nothing wrong with a good blake stitched shoe.
5) For J. Crew, I cannot comment because I am not sure who makes their shoes in Italy and what grade leathers they use.
Forget for a moment that I might be biased about Carlos Santos. I will be glad actually to send you a pair to check out. If you are staying in the more budget category for the everyday man, why not include for example a brand like Meermin which is around the 200-240$ mark?
These are just random thoughts based on a trend I see on Google all the time. For me best should include great leather, fine construction, good materials. I cannot endorse a shoe that is corrected grain leather or is full grain but taken from the belly with loose grain and will develop nasty cracks just to save a buck.
I saw someone else as the author of this article, so I am not sure how much influence you had in the final picks. But would you really take the J. Crew boot over this for a small difference in price (https://meermin.com/collections/mens-boots/products/101468-brown-suede-e) aesthetically and construction wise?
As I said, I am not here to pick a fight, but a healthy discussion and my constructive criticism as a high end shoe enthusiast (+500$). I apologize if I came in strong but as you might notice my English is well, adequate. I will keep watching your videos and reading your content because I am 5.8″ and it is very relevant and helpful to me.
Have a good weekend!
PS. Sorry for any mistakes, I wrote this off the top of my head on mobile!
Paul G says
yes, it’s very difficult to hit the right keys with your head. I’ll give you that!
Still, well done under the circumstances!
solid points 👍
Thank you for this awesome article
Just love all these different type of chukka boots available
They remain stylish, practical and versatile, A man can’t have too many of these.
A long time staple in any men’s wardrobe