A casual ankle boot that got its name from the game of polo, the chukka boot was once solely associated with off-duty Sloanes in mustard coloured trousers. Fortunately, it’s possible to scrub that out of your mind these days and 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. Opinion divides as to whether polo players wore this type of boot to ride or whether it was what they wore after a 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.

The Difference Between Chukka Boots & Desert 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 hero 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.

How To Wear Chukka Boots

Traditionally made from unlined suede calfskin on a thin sole, chukka boots today come in a wide range of fabrics and colours. Whatever you opt for, it’s a style of boot that sits comfortably in modern wardrobes and is versatile enough to be worn to the office and the pub.

“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, so you could go full-on polo chukka with pale or white trousers and a navy sweater without looking like one of Prince Harry’s boozed-up lackeys. 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.

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

If styling them up, stick to darker hues and avoid contrast colour soles where possible. “Black suede desert boots look good with a simple flat-fronted pair of trousers, a little flash of 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].”

(Related: 5 Modern Shoes All Men Should Own)

How to wear chukka/desert boots

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The Best Brands For Chukka Boots

Clarks

The purist’s choice. 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 coloured 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.

Cola Suede Desert Boot, available at Clarks, priced £95.

Clarks desert boot

Grenson

Heritage Northampton-based footwear firm Grenson has perfected classic British styles and construction methods over several generations since 1866. Current chukka models hark back to the 1930s, with fine stitching giving the boots a more formal touch. Our pick is the Marcus, a classic English-style chukka boot in snuff burnished suede and finished with a tonal heel tab.

Marcus Chukka Boot, available at Grenson, priced £215.

Grenson chukka boot

Hudson

Young fashion footwear brand Hudson offers a comprehensive and quality selection of chukka boots at affordable price points, with finishes from polished leather to traditional suede in numerous colours including classic shades of navy, tan and black. The Ryecroft style features contemporary burnished distressing on a slightly raised heel. Pleasingly Peaky Blinders.

Ryecroft Suede Boot, available at Hudson, priced £145.

Hudson chukka boot

Tricker’s

One of the longest established shoemakers in England, Tricker’s was founded in 1829 by Joseph Tricker. Nearly 200 years on the Northampton business continues to be a bastion of English shoemaking, with contemporary updates merged with classic detailing. Current chukka styles include soft handle suede uppers with contrasting white laces, but we’re a sucker for the rich chocolate hue of the Guildford model.

Guildford Chukka Boot, available at Tricker’s, priced £250.

Tricker’s chukka boot

John Lewis

Proving that good quality chukka boots needn’t cost the leg they’re going on, high street stalwart John Lewis offers great value options for less than £100. Cut from fine brushed suede that’s smart enough to dress up with a formal outfit, they’re comfortable too, packing flexible uppers and spongy sheep leather linings.

John Lewis Chumbley Suede Chukka Boot, available at John Lewis, priced £79.

John Lewis

Cheaney

One of the most respected British shoemakers on the market, Cheaney’s chukka boots have been handcrafted in its Northamptonshire factory for more than 130 years. Featuring a full fur lining for added warmth and a Goodyear welted sole that ensures the shoe will last for decades, they more than warrant their price tag.

Shackleton R Fur Lined Chukka Boot, available at Cheaney, priced £395.

Cheaney chukka boot

J.M. Weston

J.M. Weston is a French luxury shoe company founded by Édouard Blanchard in 1891, in Limoges. The brand is renowned for its handmade shoes for men, still proudly made in France, and as such commands a high price tag. Its casual chukka boot style features a rubber sole and unique sweeping stitching on the sides, so everyone knows you’ve invested in one of the best.

Brown Suede Chukka Boots, available at J.M. Weston, priced £700.

JM Weston chukka boot

J Shoes

Using only the finest materials and techniques, such as stacked leather soles and wall welts, J shoes has built a reputation for producing quality leather shoes in just 20 years. Founded in the East Midlands of England, the brand (once known as Journey Shoes) offers plenty of chukka choice. Its accessible prices give you the option of experimenting with several different colours, such as grey.

Haggerston Desert Boot, available at J Shoes, priced £125.

J Shoes desert boot

Base London

One of the most extensive chukka boot selections available on the British high street, Base London offers an entire wall of styles in every shape, finish and colour at an enticing entry price. The retailer offers sportswear-inspired updates of the traditional chukka shape, along with excellent expressions of the classic style.

Cavill Washed Boot, available at Base London, priced £79.99.

Base London chukka boot

Timberland

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

Adventure 2.0 Cupsole Chukka Boot, available at Timberland, priced £52.

Timberland chukka boot

(Related: The Men’s Shoe Care Manual)

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.

Chukka Boot, available at River Island, priced £50.

River Island

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 a chukka boot originally designed for indoor workers who would spend all day on their feet. Many styles are still made in the USA.

Classic Chukka Boot, available at Red Wing, priced $259.99 (approx £200).

Red Wing