The chukka boot is a fascinating shoe. It can be smart, almost dress-shoe like. Or, it can be casual, with a chunkier, reinforced sole. That makes for a host of styling options. Here, we’ll review what a chukka boot is, how to style it, and what socks might go best with the boot.

What is a Chukka Boot?

A ‘chukka’, loosely defined, is a boot of medium shaft and heel height, gradual slope in the upper, and four eyelets. I say ‘loosely defined’ because the origin of both the name and boot isn’t quite clear.

A ‘chukka’ is also period of a play in the game of polo (six chukkas of seven minutes and 30 seconds, with a bell rung at the seven minute mark, to be precise), so it might be associated with the equine pastime. But, as Raphael Schneider from The Gentleman’s Gazette argues in his useful history of the chukka boot, this may not actually be the case. Chukka-like boots appeared in India, yes, but also in southern Africa as far back as the late 17th century.

Regardless of the name and origin, the boots became popular among British soldiers stationed across southeast Asia and the Indian subcontinent in the late 19th century. Along with khakis and Gurkha style trousers, the Brits adopted quite a bit of style from this side of the world! (As a quick aside, be sure to read our article on matching socks with khaki pants for more details on the history of khakis and how to style them.)

James Stewart chukka boots with monkey

The boot found favor in North Africa during the Second World War, where it was prized for functionality and durability. After the War, Nathan Clark, great-grandson of the founder of the Clark’s shoe company (and himself a soldier in the British 8th army), developed a sort of hybrid chukka with a rubber crepe-like sole. He called it the ‘Desert boot’ in honor of his time with the 8th. While it took some time to catch on in the Commonwealth countries, it quickly picked up a following in the United States. Indeed, the desert boot has reached near-icon status in its 70+ year history.

Materials for Chukka Boots

While one can find chukka boots in materials from kudu to kangaroo, bovine leathers are the most common on mass-produced models. Suedes from CF Stead in Leeds, UK are common in mid-tier to upmarket shoes, like those from Carmina.

Formality of the shoe depends less on the leather and more on the last. Longer lasts with elegant, pinched waists, stacked wooden heels and leather soles are dressier than those with stubby toe boxes and thicker rubber soles. And, formality also depends on your socks.

What Socks Do You Wear with Chukka Boots?

You can wear any kind you like, but let’s consider some sartorial scenarios and where to wear what kind of sock.

Shop Socks for Dress Boots

Dress Socks for Chukka Boots

Thinner socks can absolutely be worn with chukka boots. They’ll look particularly good if you consider a few guidelines.

olive and navy striped dress socks with chukka boots

First, refer again to the last of the boot. A longer, more elegant last is best paired with a dressier outfit-and a dressier sock. If you’re looking to pair chukkas with, say, a tweed sportcoat and corduroy trousers or heavyweight chinos, a dress sock is the right call here. Or, they’re equally at home with an Oxford Cloth Button Down (OCBD for those in the ‘know’) under a cashmere v-neck sweater and some flannel pants. Or, if you'd like to try summer styling, try it with a cotton suit.

More importantly for our purposes here, a dress sock can be styled in any number of ways. Conventional wisdom dictates matching your socks and trousers to elongate the leg line. Olive trousers? Olive socks. Easy, right? But, we can get creative here-once you know the rules, it gets easier to break them.

If you’ve got a patterned jacket, try tying the socks into the subtle colors in the jacket. So: olive jacket with blue-grey overcheck. Grey flannel pants. Snuff suede chukka boots. Try a sky blue sock to accentuate both the top and bottom of the outfit. Or, in summer, it might be easy to pair brown socks with that khaki suit and unlined chukkas. True, there’s nothing wrong with that. But, try a bolder color: like peach.

Boot Socks for Chukka Boots

A boot sock works with, well, boots! But, for the best boot socks, it’s not so simple as just grabbing a thick sock and going for it.

First, consider the boot itself. A refined pair of chukkas with a thin leather upper, shaped waist, and all the other hallmarks would look rather odd with a chunky sock. So, try a more casual boot- thicker upper, thicker sole.

Next, consider the sock itself. Patterned socks are more casual and, here at Boardoom, we like a Fair Isle pattern with an intricate weave. Our Fair Isle socks are made with a custom blend of merino wool for warmth and breathability and acrylic for an ultra-soft texture that feels wonderful underfoot. They are knit right here in the USA on vintage shuttle looms-which we actually have to slow down to achieve the unique texture of each sock.

navy Fair Isle boot socks with men's chukka boots

These are most at home with some raw denim, a flannel workshirt, and a merino wool tee for a luxe-casual touch. They’re also a great candidate for a true pair of desert boots, as the wider mouth of the shoe can support a thicker sock. Socks like these could be smartened up, though, if you were to try some heavyweight chinos, an OCBD, and a Shetland wool sweater.

Shop Socks for Dress Boots

Indeed, with a bolder pattern, these socks are easy to style. They come in versatile colorways: grey heather, olive green, navy blue, and black.

As always, we’d love to hear from you. How would you wear socks with your chukkas?

Thanks for reading.

Yours in Style,

Tony Gorga
Boardoom Socks

Editorial Staff
Editorial Staff

Our editorial staff is comprised of menswear experts dedicated to providing you with helpful information. Sharing everything from style tips to sock care instructions, these gentlemen are a wealth of knowledge for both our customers and the Boardroom Socks team.

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