The Best Chukka Boots Guide You’ll Ever Read

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.”

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.

The Difference Between Chukka Boots & Desert Boots

Image Credit: Red Wing Shoes

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.

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 colours. 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.”

Image Credit: Thursday Boot Company

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-coloured 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. “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 contrast colour soles. “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.”

The Best Brands For Chukka Boots


The purist’s choice – some of the best 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 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.


Heritage British shoe brand Grenson 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 boots a more formal touch. You won’t find many better made boots.


Outdoor specialist Timberland is well known for its hard-as-nails work 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.

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.

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.