Chukka Boots: What Are They & How Do You Wear Them?

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Mens Chukka Boots - A how to wear guide

When it comes to finding casual men’s footwear that doesn’t slip into the realm of trainers, Chukka boots are a saviour.

But, you might not be entirely sure what they are and how to wear them. In this guide, we look into their legacy and how to style them at their best…

What are Chukka Boots?

Chukka boots are one of a handful of men’s footwear styles that are instantly recognizable. While the design may seem incredibly simple, they have still achieved classic status, thanks to their wearability and comfort that walks the line between being a shoe and a boot. 

billy ruffian tan chukka boots

You can identify a Chukka boot by its open front construction, which features just two or three rows of laces located at the top of the quarters. They sit at ankle height, have round toes, a slim sole with a slight heel and, in their most iconic form, are made from a light tan calfskin or suede – though darker leather styles are now just as popular. 

The origin of the Chukka boot is a little vague, with a few different theories on how and where the style was born. However, it is most likely that they caught on in India when British soldiers donned them while playing polo in their spare time – note the word ‘chukka’ also refers to a period of gameplay in the sport.

This story is supported by the fact that the Duke of Windsor was photographed wearing a pair whilst playing polo in 1924, shortly after he had returned from India himself.

Chukka Boots and Desert Boots – What’s the Difference?

As you can see, Chukka boots certainly carry a certain sense of British heritage with them. But, their story doesn’t end there. A specific style of Chukka boots, known as the ‘Desert boot’, continued to make a name for itself in the decades to come.

Desert boots were produced by the British military during WWII, adapting existing Chukka boots with a rubber sole and a light, suede upper. This footwear was preferred on desert terrain as they offered better grip and helped keep sand out of the inside of the shoe.

This differentiated them from classic Chukka boots, which to this day still feature a harder and thinner sole, with a leather upper that is typically darker in colour than the desert boot. 

How to Wear Chukka Boots

Men’s Chukka boots are best worn with a casual or smart casual outfit, but are still versatile when it comes to styling them.

They should be styled with a straight-legged trouser that should either kink slightly on the top of the shoe, or rest just an inch or two above. Black and dark brown leather Chukka boots can translate well into a more laid back business setting, too, taking you seamlessly from your office to after-work socialising.

Billy Ruffian Suede Chukka Boots

Perhaps the most iconic way to wear Chukka boots though, is simply with a pair of well-fitting jeans. Choose suede or brown leather to pair with lighter denim washes, reserving your black Chukka boots for wearing with darker denim or chino trousers.

To finish off the more casual look, pair your jeans and Chukka boots with a t-shirt, blazer or knitwear – you will find they create that perfect sweet spot of making your outfit look well put-together, but not too formal to look out of place at the pub or football. 

Billy Ruffian Chukka Boots and Fine Shoes

At Billy Ruffian, you can find carefully handcrafted leather Chukka boots created by our master shoemakers.

Shop our full men’s shoes collection to see more of our styles

Find more style advice on the Billy Ruffian Blog

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