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10 Chukkas that Offer Casual, Comfortable Style

Welcome to the comfortable side of the boot world.

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The best account of the chukka harkens back to the Raj, Britain’s former rule over India, and the polo field. It’s rumored that off-duty British soldiers would wear these ankle-high boots (similar to the polo boot, the Jodhpur) during breaks between matches — the name “chukka” actually references the periods in polo matches (called chukkas). Decades later, during World War II, British soldiers who were stationed in Northern Africa would wear these tight-to-the-ankle boots to help keep the sand out (they also replaced the leather soles with crepe soles, which stood up better to the heat and the sand). While in Burma, Nathan Clark, a British soldier and an heir to the Clarks shoe company, saw these boots on soldiers who had brought them back from bazaars in Cairo, and he liked the design. He ran with the idea after the war, implemented it into the family business, and created the now-ubiquitous desert boot.

Modern chukka styles vary, but all follow a few simple rules: ankle-height, lace-up boots with two to three lacing eyelets and a rounded toe box. They’re made from two parts of leather, traditionally unlined. Good style pairs them with either cuffed denim or custom-tailored dress slacks. The boots provide more ankle freedom and are easier to take off than traditional work boots, and the variety in styles leaves chukkas well suited for job sites (as hardy desert boots), while others pair well with a three-piece suit. Choose your own chukka accordingly.

Clarks Desert Boot

The Desert Boot is Clarks’s staple. First introduced in 1950, this Desert Boot’s 65+ years of existence, and popularity, have led to myriad colorways. They’re available in various different suede, tumbled and distressed leathers. Each pair has crepe sole and fits true to size.

Buy Now: $130

Axel Arigato Chukka

Axel Arigato, a footwear brand who Vogue recently said champions “the look of polished athleticism,” has a new take on the traditional desert boot. Their chukka sneaker has a suede upper, is lined with calf leather and is made by hand in Portugal. And if gray isn’t your color, Axel Arigato makes these chukkas in some other pretty lavish styles like alligator embossed leather, ostrich embossed leather and python leather.

Buy Now: $170

John Varvatos Hipster Chukka

All of John Varvatos’s shoes have a vintage look to them, and these chukkas are no different. They have a goatskin leather upper, a rounded toe and, maybe their most distinctive feature, rubber tire tread soles. The shoes are available in black or brown leathers.

Buy Now: $198

Red Wing Classic Chukka

The Red Wing Shoe Company has been making shoes since 1905. They use oil-tanned premium leather, which is water and stain resistant. Each shoe is Goodyear welted and comes in several upper color options including brown, gray and copper.

Buy Now: $200+

Quoddy Kennebec Chukka

Each pair of Quoddy’s Kennebec Chukkas is made by hand in Maine. They have Horween leather uppers and Vibram soles, and each pair is completely customizable; you can pick the color of its leather upper, lining, laces and sole.

Buy Now: $300

Mark McNairy Loopy Chukka

Made in England, Mark McNairy’s chukkas have suede uppers and a Goodyear welt construction, and they’re completely lined with leather. They also come with a red sole and rolled laces. If you wear any type of chino work pant, the blue uppers will slot right in with your daily attire.

Buy Now: $355

Billy Reid Indianola

Billy Reid’s Indianola shoes are beautiful. Handmade in Italy with 100 percent calfskin, they’re available in either suede or regular tanned leather. Other specs include a two-eye lace closure system and a stacked heel.

Buy Now: $395

Sandro Suede Chukka

With a beige suede upper, crepe rubber soles and simple leather lining, Sandro’s chukkas aren’t ostentatious (despite the price). They’re are made with a 100 percent cuir de veau leather and pair beautifully with dark denim jeans.

Buy Now: $425

Alden Stoneman Chukka

The Stoneman Chukka has a broad last (called the Barrie last) with a rounded toe. It has a cordovan leather upper (which possesses a natural shine) and a fully reversed welt, and it’s made in America.

Buy Now: $715

George Cleverley Nathan Chukka

All of George Cleverley’s shoes are made by hand in a workshop on London’s Royal Arcade. Each Nathan Chukka is Goodyear welted, has a soft brushed-suede upper and a Dainite sole.

Buy Now: $760

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