Even though the distinctly named Chukka boot has curious origins, it is still a staple that belongs in any dapper man’s wardrobe, due to its unique blend of elegantly casual style.

When considering the best casual boots to add to your cool weather rotation, Jodhpur and Chelsea boots likely spring to mind. Chukka boots share a few similarities with them, but they aren’t exactly interchangeable. In this article, we will dive into the origins, history, characteristics, and styling advice for the classic Chukka boot.

How Chukka Boots Got Their Name

Among all the footwear choices afforded to men, the Chukka boot certainly takes the cake for it’s unusual name. The name ‘Chukka’ is said to be derived from the seven and a half minute Polo playing period called a Chukker or Chukka. The term is itself derived from the Hindi word ‘chukkar’ meaning ‘circle’ or ‘turn’. Because there are different variations of uppers, it is unclear what exactly the original version looked like and how it got its name. One school of thought argues that Chukka boots got their name due to the resemblance to boots worn by polo players, i.e. Jodhpur boots.

Zippered Polo boots handmade in Argentina

Others believe Chukka boots were actually used to play polo although there seems to be little evidence to support this theory. Chances are the name was derived from the similarities between the two boots. This is supported by the fact that Chukka boots were sometimes worn by off-duty polo players who would slip into them after a game as they were more comfortable than riding boots.

Vintage Polo team in high polo boots

Another interesting theory is the Indian use of the word ‘chukkar’, which is also used in the context of taking a leisurely stroll or ‘turn’. Therefore, it could be entirely possible that the name was derived from the fact that the polo players preferred to stroll around in these boots after a game rather than in their polo boots.

Chukka Boots are great for fall and spring

Thus, the Chukka boot could be considered a descendant or relative of the polo boot! Whichever theory you may favor, Chukka boots have certain characteristics of their own.

History Of The Chukka Boot

Due to their similarities with the Jodhpur boot, their name and the fact that they were worn by off-duty polo players, it is safe to assume that the Chukka boot originated in India among the British army units that played the game and subsequently found its way to the west, much like the Jodhpur boot.

The Prince of Wales playing polo in 1924

The fact that the Chukka boot was first worn in the US in 1924 by the Duke of Windsor, who had previously visited India, played a little polo and had acquired a few pairs of Chukka boots only adds credence to the story. Subsequently, the Duke wore them regularly, abetting their rise to become a staple in men’s shoe closets in the West.

A fashion illustration in 1933 shows an odd jacket combination paired with Chukka boots

The British army origins are reinforced by the fact that the British army had as standard issue a type of Chukka boot worn in the desert campaign of World War II. These boots were known as desert boots and had a crepe rubber sole instead of a leather sole.

1930s Chukka boot with rubber sole that predated Clarks with yellow socks and green trousers

Whatever the precise nature of their origins the Chukka boots were designed to provide both comfort and a certain amount of style, and it was precisely because of these two qualities that they became extremely popular in the 1940s and 1950s. Chukka boots were considered a comfortable alternative to be worn as both casual and dress boots.

Marlon Brando wears chukka boots in the 1950s

One of the most ardent Hollywood fans of the chukka and desert boot was Steve McQueen, whose stardom in the 1960’s and 70’s cemented the chukka boot as a staple for the casual-cool look.

Steve McQueen Casual Style

Chukka Boot Features

Leather soles are an important feature of a Chukka boot

Because there are so many varieties, it is not always entirely clear what a real Chukka boot is and what is not. However, in studying what shoe historian June Swann had to say about the boots and considering old pictures, a Chukka boot has the following features:

Buckskin chukka boot

Lace up ankle boots. They reach the ankle and no further. Two or three lacing eyelets ; anything else is not a chukka boot Traditionally made from calfskin suede leather Rounded toe-box . Two parts each made from a single piece of leather. The quarters are sewn on top of the vamp. Open lacing. Thin soles . Soles traditionally made of leather (crepe rubber soles were later worn with desert boots) Historically unlined .

Chukka Boots Vs. Desert Boots

In 1941, while deployed to Myanmar, Nathan Clark, the great grandson of James Clark (the creator of the shoe company Clarks), noticed the chukka boot variation with crepe soles and sent sketches back home. Originally, they were commissioned as a lightweight and comfortable boot with rubber soles and sand colored leather to be worn by soldiers in their downtime. At the time, the suede uppers and crepe sole were associated with footwear only lower classes would wear, and so the Clarks Desert boot was not launched until 1950.

Clarks Desert Boot Ad from 1950

Sixty-three years later, it is probably the most common version of the Chukka boot. Priced between $60 – 150 the Clarks Original Desert Boot is popular with jeans or chinos. The quality isn’t what it used to be, but at that price you can’t ask for more. Because of its popularity, it comes in all kinds of leather and rubber colors or sometimes even fabric.

Nathan Clark with his great Clarks Desert Boots on the Left

Personally, I prefer elegant lasts with leather soles because the Clarks Desert boot has a very youthful and relaxed look that can’t be dressed up. If you have a more casual style, it might be the right choice for you.

Chukka Boots Today

Chukka boots today have become far more versatile than the originals and have been stylized to suit the times. The differences in the finer style details of the boot today determine whether they are right for business or leisure.

Uppers. Chukka boots now come in various leathers and fabrics. Synthetic fabrics, canvas, suede or faux leather / faux exotic skins Chukkas are suitable for work and casual occasions. Traditional leather Chukkas in brown suede and leather soles are suitable for casual outfits but personally, I also wear them with all kinds of blue suits. Soles. The thinner the leather soles, the finer the boots, but overall Chukka boots will never be an ideal white-collar business shoe. However, they can be worn with suits on occasion. The more casual Desert Boots often have thicker soles and rougher stitching, making them only suitable for casual wear. Colors. Although there are many color variations, Chukka boots should be brown. Personally, I prefer dark brown suede over tan, but I own both and find them equally versatile. I also choose a lace color that matches the leather for a streamlined look. Less formal Chukka boots often come with contrast stitching on the uppers but personally, I prefer it tone in tone so I can wear it more elegantly with a suit.

How to Style Chukka Boots

The Chukka boot is first and foremost a casual boot, and it should be styled as such. However, styling depends on the version of the boot that you own.

St. Crispin’s Chukka Boots with leather sole & lining

An elegant Chukka boot with a sleek last and a thin leather sole can be paired like a suede shoe and looks great with dress pants and suits. For example, I have an elegant pair of St. Crispin Chukka boots in mid brown suede leather that goes very with almost anything I wear.

Allen Edmonds chukka boots in sand paired with houndstooth flannel 3-piece suit

The possibilities of incorporating them into one’s wardrobe are endless. Dress Chukka boots with thin leather soles on an elegant last in brown can be paired with a navy or mid-gray suits and a range of other colors and patterns. For details, please look at our How to Wear Brown Shoes Guide, which also applies to Chukka boots.

Casual suede Chukka boots with crepe soles should only be worn with denim, corduroys or chinos. Avoid pairing a crepe sole Chukka boot with dress pants or a suit.

For all Chukka and desert boots, feel free to experiment with colorful and patterned socks. and different suede colors such as blue or beige – the varieties are endless. Paired with an Oxford shirt and jeans or a polo shirt, they make for a good casual outfit.

Sven Raphael Schneider wears a green windowpane jacket with a flat cap, red unlined suede gloves, corduroys and chukka boots

A brown pair goes well with autumnal trouser colors such as green, red and duskier yellows – again, experiment at your heart’s content. For an even more casual weekend look, go for Chukka boots in other materials like canvas. One can combine them with a favorite pair of old jeans and T- Shirt or khakis and a sweater.

Pinrolled jeans with desert boots

Stick to slim jeans to create a refined silhouette. The Chukka boot is a versatile boot can be worn in a variety of ways; you can use them to add variety to your wardrobe.

Chukka Boot Buying Guide

There is a wide variety of Chukka boots available on the market from an equally wide number of manufacturers. Due to their popularity, there are many manufacturers of casual chukka boots and also bespoke versions of it. Some are goodyear welted, others come with a glued rubber soles. In many cases, boots advertised as Chukka boots do not conform to the classic description of Chukkas. However one can use one’s discretion if you find a pair that may not be true in conventional sense but still suits your needs. Below is a list of a few reputable manufacturers.

Sand Chukka boots with green corduroys and burgundy and sand striped socks