The 9 Best Chukka Boots for Men in 2020

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 sneakers of the boot world because you can wear them almost anytime, anywhere. (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 10 best chukka boots for men.

Quick Take

Short on time? Here are our top three picks for the best chukka boots you can buy right now:

Read on for more info and the full list…

The 9 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: Nisolo Emilio Chukka Boot

The Emilio chukka from Nisolo is another hybrid boot, and in fact, it might better be described as a chukka-inspired boot.

The Emilio puts several twists on the classic chukka. It differs in that it features a leather sole and four pairs of eyelets (chukkas have a maximum of three pairs).

However, its ankle length and open lacing system are both what you’d see on chukkas. It’s also built a bit differently to other chukkas.

All of that said, the Emilio is an appealing boot. It’s handmade in Peru using Nubuck leather, and it comes in at the pretty affordable price of $160. In addition, you’re supporting Nisolo’s goal of ethical fashion––they ensure that their factory workers are paid fair wages.

#6: 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).

#7: 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 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.

#8: 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.

#9: 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.

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!