The chukka boot has a long history as a versatile and stylish footwear choice for men all over the world. And for good reason. These ankle-high boots hit the sweet spot for refined yet relaxed shoes, perfect for a variety of occasions. We’ll explore the timeless appeal of these boots, as well as the five best chukka boots for men, broken down by different variations of this style. Hopefully you can find a pair that fits your personality, as this style is a must-have for any gentleman’s wardrobe.
| Best Classic Option | Clark’s Desert Boots |
| Best Smart Casual Option | Beckett Simonon Laval Boots |
| Best Sneaker Hybrid Option | Jack Erwin Reade Boots |
| Best Rugged Option | Red Wing Weekender Chukka |
| Best Splurge Option | Allen Edmonds Chandler Chukka Boots |
What is a chukka boot
Chukka boots, also known as desert boots, have a rich history that dates back to the World War II era. Originally worn by British soldiers in the Western Desert Campaign, these ankle-high boots gained popularity due to their durability and comfort. Today, chukka boots have become a staple in men’s fashion, loved for their versatility, timeless design, and effortless ability to elevate any outfit.
You’ll notice from the pictures above that these are not full-on boots. The shaft only goes partially past the ankle, which gives these boots their versatility. Unlike typical boots, this shaft height allows for warmer weather wear while still offering much of the protection of a boot (hence the usage as military footwear in desert conditions).
This design feature, coupled with the 2-3 lace eyelets, creates a simple yet elegant boot structure which lends to their versatility.
Benefits of chukka boots
If you need to throw on a pair of shoes but aren’t sure what would look best, you will find yourself reaching for your chukka boots more often than you think. But their appeal goes beyond their ability to simply work with any outfit.
Depending on the specific style, the best chukka boots for men can elevate a simple jeans and t-shirt look. Most chukkas can perfectly match a button-down and casual chinos outfit, while the slightly dressier options don’t look out of place with dress trousers and a blazer. And whether your personal style leans more rugged or refined, the right pair of chukka boots can pull together the majority of your wardrobe.
You can also wear chukka boots in cold or warm weather, as their design allows for extra coverage with just enough airflow around your ankles. They really only don’t work for sweltering or freezing weather.
This classic style has been a staple in the menswear world for sometime, and their timeless appeal is likely to last for awhile longer.
Key features
Before diving into our top picks, let’s explore the essential features to look for when choosing the best chukka boots.
Material: Opt for high-quality leather or suede. These materials offer durability and comfort, and you can choose different material options based on your personal style (rugged, refined, street, etc…).
Construction: Look for boots with sturdy construction, such as Goodyear welt or Blake stitching, as they ensure longevity and easy maintenance. Some of the more casual options (like desert boots) use stitch-out welt construction, which offers a more casual appearance but are still a solid option for comfort and durability.
Sole: You can choose a rubber or crepe sole for enhanced grip and traction. These are the classic desert boot soles that provide superior shock absorption for all-day comfort. Some of the dressier options will have leather soles, like traditional dress shoes, while some of the more casual options will sport sneaker-like soles. You can select this feature based on your personal style, or you can own multiple pairs for different situations.
Fit and comfort: Chukka boots should fit snugly around the ankle and have a comfortable insole. Consider half sizes or adjustable laces for a personalized fit.
Best chukka boot options
Now we can dive into the best chukka boots for men. Based on the details of each of these options, you can figure out which pair best suits your personal style.
Clarks Desert Boots
The iconic chukka boot and the inspiration for this style of boot. The simple design of these Clarks Desert Boots gives them their charm, versatility, and stylish appeal. These can enhance almost any look. They elevate a simple jeans and t-shirt outfit, look right at home with some chinos and a polo, and can even pull duty with some dressier chinos and a casual sport coat. When considering the best chukka boots for men, every man could make use of this pair.
The spongy crepe sole and stitch out welt construction give you a supremely comfortable boot with just enough structure to offer a good level of support.
Clark’s offers these boots in a wide range of colors and materials, giving you a ton of options to best match your style. We personally favor the waxed leather or the mid and darker suede options, as these match the widest range of outfits. But let your personal style guide you, whether you want to keep it more standard or add a touch of color and flair to your looks.
They also offer the Bushacre boot, which has a similar look and construction but a different sole. This option is very affordable and a great way to test this style without spending too much money.
Other brands making a similar boot include Astorflex (made in Italy, great suede and nubuck options), Mason (the in-house Huckberry desert boot brand), and J. Crew (looks great, slightly thinner sole than the Clark’s option, which gives a sleeker look but slightly less “bounce”).
Beckett Simonon
The Beckett Simonon Laval Boots work as a great smart-casual or business casual option, with the ability to pair with dressier attire. Think of these as slightly relaxed dress shoes. While a little too dressy for a standard jeans and t-shirt look, it could work with tailored dark denim and a button down, for instance.
Wear these boots with dressier chinos and a sport coat for a nice date, with your business casual attire for a slightly more relaxed look at work, or with dressier trousers and a crewneck merino wool sweater for a perfect cool weather smart casual outfit.
These boots feature a full goodyear-welt, giving them a sturdy and durable structure. Beckett Simonon offers these in smooth full-grain leather for a more polished and dressier feel, as well as nubuck and suede options for a slightly more relaxed style.
Beckett Simonon is a relatively new direct to consumer brand that makes their shoes to order. This process keeps their costs lower (no inventory, tighter supply chains) while maintaining top level quality and durability. Check out their website if you have some time. Not only do they have a ton of other great chukka options, some dressier and some more casual, but they also have a wide variety of high quality shoes at relatively affordable prices.
Jack Erwin
For those who prefer more casual styles, the hybrid sneaker/chukka Reade Boots from Jack Erwin give a refined upgrade on your typical sneakers.
This style from Jack Erwin allows you keep all the comfort and relaxed style of your favorite sneakers while looking a little more dialed up for slightly dressier situations. Going on a casual dinner date or out for a few drinks with friends? If you would normally wear sneakers with jeans or casual chinos, reach for these boots instead, pop a chore coat or shirt jacket over your t-shirt, and automatically improve your handsomeness by 1,000%.
These are also great for those with more casual office jobs (like something in tech), so you can look a bit more professional while maintaining excellent comfort. A combo of these shoes, chinos, and a polo will keep you looking professional but not too stuffy. I also recommend these for a day trip in a city where you’ll be walking around a lot. It helps to look a little more dressed up in a bigger city. Especially if your daytime activities transition into nighttime activities.
If you’re not familiar with Jack Erwin, they pioneered the direct to consumer shoe business. And they continue to create interesting new styles like these hybrid shoes. Check them out if you haven’t yet.
Red Wing
For those who sport a more rugged style, and might need their boots to do some actual work, the American made Red Wing Weekender Chukka delivers the perfect pair of boots as per usual.
These go perfectly with a pair of broken-in denim and a t-shirt or a flannel shirt. They can also pull duty with some canvas or casual cotton chinos. Any of your more functional outerwear, like barn coats, shirt jackets, field jackets, or peacoats, will match very well with this pair from Red Wing.
For those who fit the rugged style, it’s hard to go wrong with these boots and most outfit combinations. While these are not cheap, you’re paying for top quality that will last a decade or more if cared for properly.
If you’re looking for something a little more affordable, try the brand Golden Fox. Solid looks and construction, but not quite the level of rugged appeal.
Allen Edmonds
For those with some cash and a dressier style (or a business casual need), splurging on a pair of American-made Chandler Boots from this well-respected brand will pay dividends. Of the best chukka boots for men we discuss in this post, these are the most refined and can pull duty with most of your tailored attire.
If you work in a business casual environment, consider these for a slightly unexpected twist on your normal boring office shoes. These also work well for dates at nicer establishments, with a pair of dress trousers and a button-down and/or cashmere sweater and a blazer. You could even wear these with a more casual suit (something with patterned or textured fabric).
This well-constructed and polished pair of chukka boots will turn heads. The top quality materials, classic style, and solid construction will leave you looking good for years and years with proper care.
For those of you with top dollar budgets, consider pairs from Alden, Rancourt, Loake, or Drake’s.
Conclusion
With their rich history, simple design, and unrivaled versatility, chukka boots offer a great option for any man’s wardrobe. We mentioned the five best chukka boots for men in this article, and there are a ton more options out there to fit any budget, aesthetic, and functional need. If you don’t own a pair yet, once you do make the leap, you’ll be reaching for these boots quite often.
