The Best Chukka Boots Guide You’ll Ever Read

A casual ankle boot that takes its name from the polo game, chukka boots are now replacing their origin. Once only associated with laid-back Sloanes in mustard-colored pants, it’s easy to embrace what’s one of the best easy-to-wear shoe styles around.

“The chukka boot is a simple, low-top boot with three main pieces of leather in the pattern and two or three eyelets,” says Tim Little, owner and creative director of Grenson. “The exact origin is unknown, but the assumption is that ‘chukka’ refers to a polo chukka, which is a seven-minute playing period.”

The chukka boot originated in India among the British Army units that practiced the “sport of kings” there and later found its way west, hence the thoroughbred heritage. Not that it all really matters today: it’s now one of the most comfortable and versatile types of boots to wear, paired with work pants, jeans and chinos.

best chukka boots
Image Credit: Red Wing Shoes

The Best Chukka Boots

Here’s where you can find the best chukka boots if you’re looking to add a pair (or three) to your wardrobe.


The purist’s choice – some of the best chukka boots made anywhere by anyone. In 1941, while deployed in Myanmar (formerly Burma), Nathan Clark, the great-grandson of James Clark (the founder of the shoe company), noticed the variation of the chukka with rubber soles. pancake and sent sketches home.

Originally they were ordered as a lightweight, comfortable boot with rubber soles and sand-colored leather to be worn by soldiers during downtime. It wasn’t until the 1950s that the first commercially available Clarks desert boot appeared and the style has barely changed since.

Clarks Best Chukka Boots


British shoe brand Heritage has been perfecting classic styles and construction methods over generations since 1866. Current chukka designs date back to the 1930s, with fine stitching giving the best chukka boots a more formal feel. You won’t find many better made boots.

Grenson Wendell Best Chukka Boot


MYRQVIST offers a small but high quality selection of boots with finishes ranging from polished leather to traditional suede in various colors including classic shades of navy blue, beige and black. Pay attention to the distressed effects on a slightly raised heel, which makes them pleasingly Peaky Blinders.

Best Chukka Boots

LL bean

Proving that the best chukka boots don’t have to cost the leg they go, the classic American outdoor company offers some great value options for under $120. LL Bean has created the flexibility of a running shoe with the durability of work boots that will stand up to any job.

LLBean Best Chukka Boots


Trusted American brand Rockport have dug their toes into a classic boot. Priced reasonably for such a tough boot, this smooth leather chukka will stand up to the rest. Rockport also offers the “chukka style” with more technical treds and shinier leather that pairs well with a suit.

Rockport Best Chukka Boots


A popular winter boot company aims to create powerful footwear for unstoppable individuals. Founded in 1962, the brand has since branched out into all-season footwear, and for the better. The perfect everyday boot from Sorel is waterproof, lightweight and offers superior comfort, with a vintage touch and technical features, what more could you ask for?

Sorel Best Chukka Boots


A cult classic, the Aussie brand knows comfort and there’s no compromise in this boot. With a more classic chukka shape, slippers and sport styling, there’s a versatile UGG for every foot. The retailer offers activewear-inspired updates to the traditional chukka shape, as well as excellent expressions of classic style.

UGG Best Chukka Boots


Outdoor specialist Timberland is well known for its nail-hard work boots, but it also happens to be a contemporary range of the best chukkas that feature Timberland’s distinctive upper. These styles have more eyelets than usual, reflecting the signature Timberland pattern in different finishes and colors.

Timberland Best Chukka Boots

River Island

At the more affordable end of the high street, it’s possible to sacrifice real leather for something faux and get a wider selection of classic and contemporary silhouettes in the process. River Island has no shortage of great colors and finishes that you won’t have to choose from.

River Island chukka boots in brown leather

red wing

Known to last a lifetime, Red Wing prides itself on the quality craftsmanship of its boots. Located in southwestern Minnesota, the brand offers an American version of this English style with the best chukka boots originally designed for indoor workers who would spend all day on their feet. Many styles are still made in the USA.

Red Wing Best Chukka Boots

How to Wear Desert Boots

Traditionally made from unlined suede calf leather on a thin sole, chukka boots today come in all kinds of fabrics and colors. Whatever you choose, it’s a style of boot that fits comfortably into modern wardrobes, versatile enough to wear to the office and the pub. It’s one of the best boots to wear with jeans, but you can also play on the style’s bourgeois heritage.

“They are primarily known as a smart-casual crossover, but that depends on the leather. A lightweight suede can create a very different feel than a highly polished black version,” says Little. “They tend to look best with a narrow pant leg, either folded over the shoe or nowadays more likely about an inch above the boot.”

Chukka boots are most commonly found in shades of brown, but if you want to avoid looking like a pre-Meg Prince Harry, steer clear of light-colored pants. To avoid any horse-riding connotations, the boots pair best with knitwear and casual pants, says John Lewis men’s shoe buyer Philip Goodwin.

Thursday Boot Company chukka boots
Image Credit: Thursday Boot Company

“Chukkas go just as well with jeans as they do with chinos, and more formal versions help dress down a suit for a more casual look,” he says.

Want to style them? Stick to darker shades and avoid soles in contrasting colors. “Black suede chukka boots look great with simple flat-front pants, a little sock zipper and a button-up shirt,” adds James Datlen, men’s buyer at footwear retailer Schuh.

“For a more casual day-to-day outfit, you can opt for selvedge denim or a pair of Alpha Dockers. A crew neck sweatshirt works well too.

Thursday Boot Company chukka boots
Image Credit: Thursday Boot Company

Chukka Boots FAQ

What is the difference between desert boots and chukka boots?

Confusingly, all desert boots are chukka boots, but not all chukka boots are desert boots. The easiest way to tell the two apart is to look at the sole.

The Desert Boots, which were adopted by British forces during World War II and later exported to the UK by British footwear brand Clarks, feature a natural crepe rubber sole.

This spongy material (made of layers of latex) makes the style more comfortable and practical, but also more relaxed. If you don’t have a crepe sole, you wear a chukka boot.

What are chukka boots for?

These days, chukka boots are used for everything from errands to a night out on the town to a day sitting at the office. They came into fashion as casual wear and were originally used by British Army units to play polo.

Are chukka boots good for winter?

One of the best reasons to invest in a great pair of chukka boots is that they truly are an all-weather shoe. Be careful, however, if you opt for a suede pair. If you don’t treat your suede boots before stepping in the snow or rain, you could very easily ruin them for good.

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