The Best Chukka Boots Guide You’ll Ever Read - Fashion Daily Tips

The Best Chukka Boots Guide You’ll Ever Read

A casual ankle boot that got its name from the game of polo, chukka boots now supersede their origin. Once solely associated with off-duty Sloanes in mustard-colored trousers, it’s easy to embrace what is one of the best easy-wearing footwear styles.

“The chukka boot is a simple, low-ankle boot with three main pieces of leather in the pattern and either 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 period of the game.”

The chukka boot originated in India among the British army units that played the ‘Sport of Kings’ there and subsequently found its way to the west, hence the thoroughbred heritage. Not that any of that really matters today: it’s now one of the most comfortable and versatile types of boot to wear, pairing with work trousers, jeans and chinos alike.

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 chukka boot variation with crepe soles and sent sketches back home.

Originally, they were commissioned as a lightweight, comfortable boot with rubber soles and sand-colored leather to be worn by soldiers in their 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


Heritage British shoe brand has perfected classic styles and construction methods over several generations since 1866. Current chukka models hark back to the 1930s, with fine stitching giving the best chukka boots a more formal touch. You won’t find many better-made boots.

Grenson Wendell Best Chukka Boot


First-foot-forward MYRQVIST offers a small but high-quality selection of boots with finishes from polished leather to traditional suede in various colors including classic shades of navy, tan and black. Look out for distressed effects on a slightly raised heel, making them pleasingly Peaky Blinders.

Best Chukka Boots

L.L. Bean

Proving that the best chukka boots needn’t cost the leg they’re going on, classic American outdoors company offers great value options for less than $120. L.L. Bean has created the flexibility of a running shoe with the durability of work boots that will stand up to any job.

L.L.Bean Best Chukka Boots


American trustworthy brand Rockport has dipped their toes into a classic boot. With a reasonable price tag for such a durable boot, this smooth leather chukka will stand up to the rest. Rockport also offers the ‘chukka style’ with more technical treds and higher shine leather that would pair 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 best. Sorel’s perfect everyday boot is waterproof, lightweight, and provides superior comfort, with a little vintage twist and technical fixtures, what more could you want?

Sorel Best Chukka Boots


A cult classic, the Australian brand knows comfort and there is no compromise in this boot. Coming in a more classic chukka shape, slipper, and sport-style, there is a versatile UGG for every foot. The retailer offers sportswear-inspired updates of the traditional chukka shape, along with excellent expressions of the classic style.

UGG Best Chukka Boots


Outdoor specialist Timberland is well known for its hard-as-nails work boots, but it also turns out a contemporary range of the best chukkas that feature the distinctive Timberland upper. These styles have more eyelets than usual, reflecting the Timberland signature model in various finishes and colors.

Timberland Best Chukka Boots

River Island

At the more affordable end of the high street, there’s the option to sacrifice real leather for something faux and gain a greater choice of classic and contemporary silhouettes in the process. River Island is not short on great shades and finishes that you won’t be forced to choose between.

River Island Brown leather chukka boots

Red Wing

Said to last a lifetime, Red Wing prides itself on the build quality of its boots. Located in Southwest Minnesota, the brand offers an American take on this English style with the best chukka boots that were 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 Chukka Boots

Traditionally made from unlined suede calfskin on a thin sole, chukka boots today come in all manner of fabrics and colors. Whatever you opt for, it’s a style of boot that sits comfortably in modern wardrobes, versatile enough to be worn to the office and the pub. They’re one of the best boots to wear with jeans, but you can also play on the style’s upper-class heritage.

“They are known mainly as a smart-casual crossover, but it does depend on the leather. A light suede can create a very different feel from a highly polished black version,” says Little. “They tend to look best with a narrow trouser leg, either kinked on the shoe, or nowadays, more likely an inch or so 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, dodge light-colored trousers. To avoid all connotations of horsing around, the boots pair best with knitwear and casual trousers, says Philip Goodwin, men’s footwear buyer for John Lewis.

Thursday Boot Company chukka boots
Image Credit: Thursday Boot Company

“Chukkas look equally good with jeans or chinos, and more formal versions help dress down a suit for a more relaxed look,” he says.

Want to style them up? Stick to darker hues and avoid contrasting color soles. “Black suede desert boots look good with a simple flat-fronted pair of trousers, a little flash of a sock and a button-up shirt,” adds James Datlen, a men’s buyer for footwear retailer Schuh.

“For more casual, day-to-day wear, you can go with some selvedge denim or a pair of Dockers Alpha. A crew neck sweatshirt works well, too.”

Thursday Boot Company chukka boots
Image Credit: Thursday Boot Company

FAQs About Chukka Boots

What’s 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 by looking at the sole.

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

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

What are chukka boots used for?

Nowadays, chukka boots are used for everything from running errands to a night out on the town, to a day sitting in the office. They came into fashion as casual wear, and were originally used by British army units to play the game of polo.

Are chukka boots good for winter?

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

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