Versatile, Timeless and Sturdy as Hell: The Best Chukka Boots for Men in 2023

Dust off those desert boots

March 30, 2023 11:17 am
a collage of Chukka Boots on a grey background
A longstanding staple of the dapper man's wardrobe, the best chukka boots for men are a timeless investment
InsideHook/Getty Imagees

Nota bene: If you buy through the links in this article, we may earn a small share of the profits.

Chukkas are more than just a boot, more than just a spring essential — they’re a genuine jack of all trades. Originally a WWII military design, the style has since been streamlined for the office and the weekend alike; they can dress down a suit, dress up some chinos, and they even play nicely with jeans. In fact, the best chukka boots are the single most functional pair of footwear, even moreso than the hallowed white sneaker, we can think of. So many guys (Obama and Bourdain, to name a few) swear by them that they’ve been integrated into the standard menswear uniform. All of this to say, you need a pair.

What Is a Chukka Boot?

The idea for Chukka boots reportedly originated in the midst of World War II as suede beater of a shoe utilized by British infantry in the dusty middle-eastern campaigns of the ’40s, before being co-opted into an everyday style by Nathan Clark (of Clarks, maker of the OG Desert Boots).

Typically crafted from a suede or leather outer and spongy crepe sole, the boot’s simple design hits right above the ankle, placing it somewhere between beat-up Converse and a full-blown dress boot. It’s fixed from a one-piece upper and unadorned vamp that provides adequate coverage from the elements, making it ideal for transitional weather and uncertain conditions. Modern variants have introduced additional tech and specs — Goodyear-welted soles, innovative uppers and deconstructed finishes have all revolutionized the stiff Desert Boot in recent years.

How to Wear Chukka Boots:

As we’ve mentioned, the beauty of the Chukka lies in its boundless versatility. While you’ll want to operate within the standard style parameters for boots (see: socks are a must, shorts are a no-go, and leathers should probably match), the rest is up to you. Jeans and a cable knit imbue a Chukka with some preppy polo flair, while a soft-shoulder suit and a burnished leather desert boot is the outfit to beat at many a spring wedding. Really, the way you style them is up to you.

Which Chukka Boot Is Right for Me?

Despite its prolific status, the are hundreds of Chukka boots beyond Clarks Desert Boot, with everyone from classic American designer Todd Snyder to San Francisco-based retailer Everlane offering their own take on the style. As such, we’ve taken it upon ourselves to break down the appropriate footwear for every situation. Below, the best Chukka boots for men in 2023.

The Best Chukka Boots in 2023:

Move over Clarks — there’s a new Chukka in town. Todd Snyder’s Nomad Boots are the platonic ideal of a do-everything desert boot, set on cloud-esque foam above a 12mm premium rubber sole and finished with a handcrafted Italian suede upper. They match with anything, from suit on down, and this pair in particular looks luxe enough to keep you in good graces.

Chukkas are the holy grail of office shoes: dressy enough to wear to work but comfortable and laid back enough to wear to happy hour. The Astorflex Greenflex is a great example of how good the gift of the office Chukka can be, with soft European leather, a 100% rubber outsole and a Steve-McQueen-mets-corner-cubicle vibe.

A cousin of the iconic Desert Boot, the Bushacre 3 may not include top-of-the-line materials, but at a cool $75, any quality-related transgression is quickly forgiven. Plus, the footbed is as just as cushioned its Clarks brethren, meaning you don’t have to sacrifice an ounce of comfort (or your heels to blisters) to reap all the benefits a Chukka provides.

They may be a desert boot by name, but Everlane’s hybrid footwear looks and feels more like a high-top than a chukka boot. They read classier than your Dunks, but if you can’t go without your sneakies for even a day, you’ll want to opt for these springy suede joints. Plus, they kinda look like Loro Piana’s version…at a literal fraction of the price.

J.Crew’s latest collab with Massachusetts-based Alden proves that their transformation is complete: just look at this absolute specimen of a Chukka. The boot is handcrafted in the USA from moldable suede uppers and leather-lined insoles and Goodyear welted — this means you can resole them for a literal lifetime of wear — all while maintaining that dressy, outer-stitched look.

More Chukka Boots That We Love:

Clarks Desert Boot is the undisputed OG of Chukkas, and for good reason — it’s a perfectly concocted mixture of rugged functionality and timeless style.

Slippers can be Chukkas, too, you know.

Tired: a lame old Chukka. Wired: the lugged GREATS Henry that’ll put most combat boots to shame.

Rhodes Tyler Boot is crafted in Leon, Mexico, and every ounce of craftsmanship bleeds through in this rugged chukka’s quality finish.

Ghiaia Cashmere, run by ex-Cucinelli designer Davide Baroncini, is all about quality and sophistication, which probably explains why their deconstructed Canvas Desert Boots captures a nautical spirit while delivering a premium finish only made-in-Italy wares can provide.

Nothing to see here: just a classic suede Chukka straight out of the a ’90s J.Crew catalog.

Heavy bull denim twill isn’t the standard Chukka material, but Seavees’ does the style justice.

Cole Haan’s ZERØGRAND line resembles moon shoes more than the British Eight’s dusty desert boots, but the waterproof leather and TPU-outsole make them ideal for soggy commutes.

Sperry gave the Chukka a little Virbram-soled boat shoe makeover, and we can’t say we’re particularly mad about it.

Part Chukka and part rough-and-tumble saddle, Taylor Stitch’s handmade Rambler has a thick lug sole and a 4-oz. mushroom waterproof suede exterior, making it much more of a bruiser than its suede competitors.

The InsideHook Newsletter.

News, advice and insights for the most interesting person in the room.