The Versatility of Well-Loved Chukka Boots

No men’s shoe collection can be complete without the loveable chukka boot. Initially thought to have originated from the middle east, where the British army found a liking for them, the chukka boot was first made popular in the 1920’s when the Duke of Windsor was seen wearing his own pair.

chukka boot

Why is it called a chukka?

Before I tell you why the chukka boot is such a staple in every man’s (and some women’s) wardrobe, we should probably discuss where the name is said to have come from. ‘Chukka’ is a term used in polo for the time of play; not very interesting, I know. However, it is thought that these loveable boots share some similarities with polo player’s footwear at the time, so I suppose it is relevant to discuss.

It has also been mentioned by many fashion enthusiasts that the term for this staple boot has some relevance to the term in India ‘chukkar’, which means to take a stroll. Both ideas seem to fit well, so it could really be a combination of both. Anyway, that’s your history lesson for today, let’s discuss this essential piece of footwear in a way that might be more relevant for you.


This boot has been widely adored because of its versatility; it is not quite a boot and not quite a shoe, so it makes for a great option when styling most outfits. Typically, chukka boots have thin soles, rounded toes and sit at the height around your ankle. They come in such a varied style nowadays but originally would be either brown suede or leather in material and colour.

These laced up boots are a feature in most male’s shoe collection. My partner has a “smart” pair and a “casual” pair; I won’t lie to you, they both look smart and casual at the same time, but I think it is more about the colour for him. His smart pair are darker brown and can look really swanky if he buffs the leather and his casual pair have that well loved look, with a worn suede material. Typically, he rocks the swish leather chukkas on date nights and for job interviews and I must say, they really do transform an outfit.

Picture this, slightly worn faded jeans and a Carhartt checked shirt. This ensemble screams smart-casual, but add your partner’s favourite cologne, his hair tied back and stick on his best Loake’s leather chukka boots and suddenly, he could pull this look off in a Michelin star restaurant with a strict dress code. Not one to buy designer very often, the Carhartt shirt was a gift and the Loake’s chukkas were £1.50 from a charity shop!

I could not believe our luck finding a pair of size ten chukkas from such a well-established British shoemaker during one of our thrifty shopping weekends. Probably one of the best finds we have had when perusing the charity shops on the high street. Perhaps it was because we were living in a relatively wealthy neighbourhood at the time, full of Barbour jackets and young girls who owned their own horses, which meant the charity shops were packed with designer brands and plenty of items that hadn’t been worn at all.

Style of Chukkas

Aside from the steals on our shopping trips, the second pair of chukkas my partner has probably fit more in the subcategory of ‘desert boots’. This style of chukkas has taken the globe by storm over the last few years, with even plenty of females adopting the casual boot style. They keep all the noticeable features of the chukka boot, such as thin sole and two or three lace holes but their sole is also crepe rubber.

chukka boots

This slight variation in the chukka boot was first made iconic by British shoe company Clarks and remains one of their best-selling shoes to date. At the time, the materials used were associated with the lower class however Clarks was able to revolutionise the desert boot to suit everyone.

Whilst I am a fan of all variations of the chukka boot, the desert boot can only really be worn casually. The crepe rubber sole does not work with a suit and certainly wouldn’t look right at a wedding or christening. This kind of casual sole is still better than trainers so if you are looking for that in between smart – casual look, they may work.

If you want to rock the casual look, ideally pairing them with jeans is a definite. For super casual, try blue straight leg jeans paired with any style of t shirt, shirt or jacket and a relaxed desert boot. If you want to find that middle ground between smart and casual, try pairing your suede chukkas with black jeans and a comfortable shirt; add a splash of your favourite scent and away you go. Alternatively, for a smart style, I would strongly suggest avoiding the desert boot. Stick to the traditional brown leather chukkas to pair with a pin stripe suit and you will smash the boardroom and win all the clients, whilst feeling confident and looking suave.

The suede style desert boots have recently become a popular choice for women too. I love pairing my blue suede boots (no Elvis reference intended) with black tights and a cute colourful dress for something different. Sometimes I swap out my Dr Martens for my brown desert boots to pair with baggy jeans for a laid-back aesthetic. They especially look great with loose fitting cardigans and plain tees too.


So, the title of this article really is the truth. Chukka boots are extremely versatile and even allow you to play with your styles day by day. If you typically find yourself in a fashion rut, buying yourself a pair of chukkas could help revamp your whole wardrobe. You could find yourself inspired by the British Mod who loved to rock a chukka on their Vespa or maybe Daniel Craig’s role in Quantum of Solace filled you with inspiration on how to look as good as a spy in your own chukkas. Whatever your preference, there is a chukka boot for every look, so get shopping!