The history behind Chukka vs Chelsea | Style the right boot this autumn

The four seasons of the year; winter, spring, summer and autumn. Although the summer blues have descended upon us, it’s not all doom and gloom. The start of autumn marks the stage where it is finally acceptable to wear those big winter coats, scarfs and best of all your favourite pair of boots.

Shoes always finish an outfit off, they are the statement piece to a man’s outfit, so it’s not surprising that so many men choose to style a pair of Chukka or Chelsea boots each autumn and winter. But what is all the fuss about? Where did they come from? What are the differences between chukka and Chelsea and how do you style them right?

Experts in gentlemen’s fashion and retailers of high-quality leather boots, Frank Wright is here to provide us with an insight into the differences between the boots and how to pair them with AW 17/18 trends.

The lace up Chukka

Although the name ‘Chukka’ sounds like it was pulled out of thin air, there is actually some science behind it. It is thought that the name for this style derived from polo, where a ‘chukka’ is a seven-minute period of the game – although it is uncertain whether the shoes were worn throughout the game or by the players afterwards.

Following World War II, where a variation of the Chukka boot was used for soldiers marching through desert terrain, the boot was introduced into every man’s wardrobe. They went on to become a major fashion piece in England during the 1950s. Ever since, they’ve remained at the forefront of men’s fashion – wearable for casual or smart occasions.

Also known as desert boots or turf boots, a Chukka boot is recognisable by an ankle length cut and pairs of eyelets for laces. They generally have a classic, plain toe design and an open lacing system.

This style of shoe is usually crafted from calfskin or suede but leather can be used too – making the shoe more durable in the colder months.

The traditional Chelsea

Just like the name ‘chukka’ there is also some history behind the name ‘Chelsea Boot’. The Chelsea boot dates to the Victorian era where it is believed they were designed by the Queen’s personal shoemaker – J. Sparkes-Hall. Their popularity rose in the 1960s in Great Britain as they became linked with the mod scene. They also were associated with King’s Road, a street in Chelsea, and it is thought that this is where their name derived from. Celebrities such as the Beatles and the Rolling Stones helped boost their popularity.

Similar to the Chukka boot, the Chelsea style of shoe is ankle length and generally made of suede or leather. It is characterised by its iconic elasticated panels that allow the shoe to slip on and off, and often there is a tab of fabric on the back of the boot. The fit of the shoe should be a close fit, and any flexibility in the shoe should be in the side panels – not in the instep.

How should you style for AW17/18?

Both the Chelsea and the Chukka boot are versatile styles that are suitable for many occasions. But how should you style the boots to keep up to date with the AW 17/18 collections?


The Chukka boot is an ideal alternative to more formal leather lace-up brogues if you’re opting for a casual look.

When matching the shoe to the occasion, look closely at the finer details of the boot. Synthetic fabrics and some suedes are more suited to a casual event whereas leather and smarter suedes can be worn more formally. Also examine the sole – the thinner the sole, the finer the shoe. More casual Chukka books can be recognised by a thicker sole and rougher stitching, giving a quirkier appearance.

It is likely that the Chukka boot will be suitable for your style, although they do sit better with narrow legged trousers. Some men prefer a shorter hem; pair with patterned socks for a stylish, casual outfit. Designs on the catwalk for this season included oversized jackets and knitwear. Wear with an extra-long, smart jacket with dark jeans and brown Chukka boots to keep practical and on trend.

For a smarter look, match a rounded toe, brown Chukka boot with a navy or mid-grey suit. Or, couple the same boots with moss green trousers – a prominent colour on the AW 17/18 catwalk.


Like the Chukka boot, the Chelsea boot is versatile and compatible with many items in your wardrobe. Although suede is often the material of choice for this style, to protect from the colder weather and rain, opt for a leather boot to get you through the autumn and winter.

A big trend for this autumn is roll necks. Pair a dark roll neck jumper with skinny jeans and a Chelsea boot for casual evening attire. Or for a smarter look, a grey suit with brown leather Chelsea boots and a matching briefcase.

This year, many designers went against the grain and created tailoring that wasn’t traditionally black or navy. Extend the colours in your wardrobe with an autumnal coloured suit such as burgundy or blue and pair with Chelsea boots – make sure that the trousers sit just over the top of the boot to show off the shoe but remain smart.