The chukka boot is a simple yet versatile boot that looks good with almost any outfit. Here are the best chukkas you can buy right now.
Chukkas are kind of like the
If you want a comprehensive guide, check out our article on how to wear them.
Even better, you can choose from more casual or more formal chukkas to suit your needs.
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 right now.
Quick Take
Short on time? Here are our top three picks for the best chukka boots you can buy right now:
Our Pick
Budget Pick
Handmade in Portugal and offered by Huckberry, this is an affordable and stylish option available in bone, coffee, or sand color options.
Buy Now
Upgrade Pick
Read on for more info and the full list.
The Best Men’s Chukka Boots
No matter your budget or style preferences, you’ll find a pair of chukkas on this list that will work for you.
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 probably fit right into your wardrobe. They’re also nice for a laid-back smart casual look (or just straight-up casual looks).
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.
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.
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.
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 unstructured silhouette, sneaker-style cotton laces, and rubber sole give this chukka a decidedly casual look and feel.
Typically available in grey or brown, these chukkas will go with pretty much every pair of casual pants you own.
No, these aren’t artisanal-quality Goodyear-welted boots, but you’re getting a lot of value for the price (especially if you can pick them up on sale).
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 leather, 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.
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.
Huckberry Mason Chukka Boot
Huckberry’s an incredible brand for guys. Rhodes Footwear, one of Huckberry’s several brands, has their own take on the chukka.
Handmade in Portugual, the Mason Chukka Boot is one of the more affordable options on our list. These boots have a suede upper, a crepe rubber sole, and cotton laces.
Choose between three colors: bone, coffee, or sand.
Astorflex Greenflex Chukka Boot
The lovechild of an Astorflex-Huckberry collab, the Greenflex Chukka is only available at Huckberry.
These boots are made by sixth-generation shoemakers in Northern Italy, so you know you’re getting a quality-built boot.
While on the more casual end of the chukka formality spectrum, these boots can be dressed up, but won’t really work with all but the most casual suits.
Beckett Simonon Laval Chukka Boots
Unlike the other boots on our list, Beckett Simonon’s Laval Chukka Boots are made-to-order, meaning that the customer receives the new kicks straight from the factory. This business model helps to cut down on middle-man costs, and part of the saving is passed on to you.
For what you’re getting — hand-cut Italian full-grain calfskin leather, blake-stitch construction, leather insoles, and more — $239 is an incredible price.
With their beautiful profile, these boots can easily be worn with a sport coat.
Nisolo Everyday Chukka Boot
While Laval Chukka Boots are classically styled, this next pick has a bit more character.
The Everyday Chukka Boot from Nisolo has an Old West feel with modern details. To me, the Everyday Chukka is a bit of a hybrid boot rather than a pure chukka.
The soles of these boots are especially interesting as they’re made from vegetable-tanned leather but have shock-absorbing, rubber sole savers. I’m not sure if this kind of sole can be replaced, but they look quite eye-catching.
If you’re an ethically-minded shopper, you’re in luck because Nisolo makes considering your impact easy with their “Sustainability Facts” page which details the conditions of workers and the impact of the boots on the planet, scoring the boots across 200 sustainability metrics.
Drake’s Snuff Suede Murphy Goodyear Welted Chukka Boot
If money is of no object to you, the Snuff Suede Murphy Goodyear Welted Chukka Boot from Drake’s is a beautiful made-in-England boot.
The Murphy Chukka is a great choice if you demand perfection. The details are expertly executed here which, combined with some of the best materials, make for top-of-the-line chukka.
With Dainite soles and soft-tailored luxury suede, these are some nice boots.
Meermin Castoro Ultraflex System Chukka Boot
Meermin’s sleek, leather-soled Ultraflex System Chukka Boot is said to be extremely comfortable.
The Ultraflex System is a new spin on Goodyear welt construction. In this case, the welt is actually stitched to a structural insole, overwhich a leather-lined memory foam removable insole is placed.
With this system in place Meermin claims that “the wearers foot is almost 3cm comfortably separated to the ground — as opposed with a cemented shoe which can be just a few millimeters.”
Not only is it comfortable, this boot is made to last as it’s fully rebuildable.
Conclusion
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!
