12 best chukka boots for men

When British soldiers marched through the deserts of Egypt and Libya, they did so in comfort and style. Today, the classic chukka boot is rooted in world history and was a popular style of footwear for men from the 1940s to the ‘60s. At the turn of the century, while many fashion trends died out, the chukka boot remained strong, especially in the United Kingdom.

Made from calfskin or suede, the chukka is a stylish, unlined ankle-high boot that sits on a leather sole. Some variations may have a rubber sole, though all tend to have two to three pairs of eyelets for matching or complementary laces. Another variation, known as the desert boot, calls inspiration from the chukka of World War II and is always designed with a rubber sole and suede upper.

Regardless of the design, chukkas are a timeless boot that completes any outfit without sacrificing comfort. Whether you’re looking for a desert-style chukka or want to strut around in a modernized iteration of the civilian chukkas of the mid-20th century, these 12 styles will suit you well.

Manufactured and stitched by master craftsmen, these chukkas are a fine addition to any wardrobe.

clarks chukka boot leatherField Chukka Boots

For the man with a need for style and comfort, this chukka, available in olive or a very striking, deep red, covers the three “S’s” – sleek, simplistic, and stylish. Two eyelets and matching stitching ensure all of the focus is on the clean design and the expert craftsmanship. A thicker outsole with crepe texture on this Italian-made Brooks Brother’s chukka provides for maximum comfort with each step without sacrificing the boot’s overall aesthetics.

Paired with a nice pair of slacks, these finely crafted chukka boots are enough to complete any outfit.



clarks mens bushacre beeswax leather boot shoeBushacre 2 Chukka Boot

Clarks has a message for any man looking for a stylish boot to wear around town – it doesn’t have to be overcomplicated with too much lacing and an oversized outsole. This chukka boat is simplicity at its best, with two eyelets, a very clean leather design, and a shock-absorbing outsole that is just thick enough to be comfortable and practical for a boot.

Available in black leather and grey leather, Clarks’ Bushacre 2 is all about comfort and style. On the outside, a look uncluttered by unnecessary design elements. On the inside, an insole lining of suede to nestle the wearer’s foot and keep it cozy.


kenneth cole reaction desert sun chukka bootDesert Sun Leather Chukka Boot

Now here’s a chukka that wants to be taken out on the town. Three eyelets are all these sleek, leather boot needs as the expert white stitching contrasts the darker brown color of the upper for a visually appealing footwear. The black leather option is less about the contrast and more about being as dressy as possible without sacrificing comfort.

Kenneth Cole’s Desert Sun chukka is outfitted with elasticized ankle gores for a smooth and more comfortable fit. The cushioned insole amplifies that comfort while the harder rubber outsole checks off the box for practicality.

Whether you’re out on the town or on your way to a business meeting, this chukka is ideal for either scenario.


clarks mens broyd chukka bootClarks Broyd Mid Chukka Boot

Want to feel like a rustic cowboy but don’t want to deal with the nuisance of having to wear real cowboy boots? Then you’ll absolutely want Clarks Mid Chukka in brown leather. It couldn’t look more rustic if it tried. If it’s style you need, however, switch over to black leather and you’ll have the versatile casual look you need for an evening of dressing up or a day of dressing down.

Imbued with Clarks’ “Cushion Plus” technology, the Broyd Mid Chukka is comfortable no matter which style you go for. Three eyelets allow for a snug fit to keep it from slipping and the OrthoLite footbed makes for a comfortable step each time. The outsole is a simple brown rubber with a black stripe for the style.


chippewa dress chukka boot for menDress Chukka

Chippewa found a way to utilize the silhouette of a chukka in its line of durable, classic boots. There’s no mistaking this tan beauty for anything other than a stylish, rugged boot. The timeless design is a Goodyear leather welt that promises lengthy durability while a Vibram V-Bar outsole means this chukka will stand up to most conditions. Even the wax-coated laces are built to last!

You won’t have to trot around uncomfortably at any point in this boot as it was crafted to not need breaking in. Whether you’re doing heavy lifting or want a nicer boot to sport while out and about, the Dress Chukka is a great option that will be with you for a long time coming.


Cole Haan Benton Welt Chukka Boot black for menCole Haan Benton Welt Chukka Boot

With this simple chukka design, Cole Haan delivers on an option perfect for casual wear and for a more elegant night out. There’s really nothing to it – just two eyelets, a simple stitching in the upper to give it shape, a trim at the ankle and back panel to contrast the suede black upper, and a sleek black leather outsole designed for comfort and style.

The Benton Welt Chukka Boot makes no qualms about what it was constructed to be: a comfortable, dressy article of footwear that’s both visually appealing and made to last. Available in wide width and a vast selection of sizes, this chukka will work for every type of man.


Rockport Men’s Essential Waterproof Chukka Boot in blackRockport Men’s Essential Waterproof Chukka Boot

Not everybody wants to spring for boring dress shoes that can only be worn on those fancier occasions. Loafers are stylish, but they’re not an “everyday shoe.” That’s where Rockport’s Men’s Essential chukka comes in, especially in this all-black coloring.

Sure, you can slip on this four-eyelet chukka for a simple stroll, but its stylish all-black design helps it look a lot more elegant than your average casual chukka. Black stitching blends into the upper leather construction, which flows perfectly into the black rubber outsole. The lightweight comfort system is all about absorbing the shock of each step.

It may not have any flair or pizazz, but Rockport’s chukka wasn’t designed to be showy. It’s all about comfort and class.


Rocky High Gloss Dress Leather ChukkaRocky High Gloss Dress Leather Chukka

You’ve been invited to your best friend’s wedding and asked to be in the bridal party. You know that means you’re going to have to splurge on a suit and dress shoes, but you’ve never liked the traditional style of dress shoe. The toes are too pointy, the finish is bland, and they’re simply not unique enough for you.

Lucky for you, you don’t have to go the traditional route with Rocky High Gloss Dress Leather Chukkas available. Like any dress shoe, this leather chukka has a glossy finish that makes it look more formal. A cushioned heel provides comfort for when you hit the dancefloor while the Pro-Cell rubber outsole keeps your feet on the floor.

The entire design is even more comfortable than dress shoes, allowing you to wear them the whole evening without the typical throbbing in your foot.


Born Men’s CristianBorn Men’s Cristian

Sometimes you just want footwear that’s easy to put on and incredibly casual. Rather than go with a typical sneaker, you can go for this stylish chukka. Though it may look like a sneaker, everything about it screams “classic chukka.” From the suede upper to the thick rubber outsole, Born Men’s Cristian athletic chukka is a perfect mix of authentic design and staple comfort.

The 1” sole cushions the bottom of your foot while the leather lining adds another level of comfort. Three eyelets make for an easier lacing than the average sneaker while still coming off as very casual.


Men’s Authentic Original Wedge ChukkaMen’s Authentic Original Wedge Chukka

There’s nothing nicer looking than a handcrafted, tan leather boot – that is, of course, until the chukka version was introduced. This classical style is stitched to perfection, every piece of thread contrasting the darker upper of the low-ankle boot.

Made from genuine hand-sewn leather and suede, this original chukka wedge is comfortable without giving up visual appeal. The outsole heel cup is made to absorb shock for maximum comfort and is made to avoid keep traction in wet and dry conditions.

It’s practical and attractive – what more can you ask for in a boot?



straightset chukkasStraightset Chukkas

Want a chukka but don’t want to dive into anything more on the formal side of footwear? Lacoste delivers the perfect option for the casual shoe with this Straightset Chukka. Available in black on black or navy on a white sole, Lacoste’s flair for style and pleasing aesthetics ensure that this chukka is casual without being juvenile.

Cotton lining provides for a breathable chukka and a more traditional lace-up ensures a more comfortable and snug fit. So people know you have good taste, Lacoste brands the boot with its signature croc logo. It’s small, however, so don’t worry about feeling like a walking billboard.

The rubber outsole, available in black or white, lets the wearer feel like they’re in a more comfortable sneaker without taking away from the leather upper.


TOMS Chukka Boot in black for guysTOMS Chukka Boot

TOMS may be better known for its whimsical and playful designs, but this chukka is all about aesthetics and practicality. Though it sports the stylish look of a traditional chukka, TOMS version of the classic footwear is made for the rugged man.

This versatile boot can tackle the big outdoors while also providing a slightly dressy footwear for when the occasion calls for it. Made out of full-grain leather or cotton twill, TOMS’ chukka is breathable, flexible, and comfortable with a flannel lining that seems to hug the wearer’s foot.

A thermoplastic outsole sticks to the theme of the “casual adventurer” and provides for increased durability, support, and traction. For an easier fit, each of the five designs sports a convenient pull-up tab.