I have always been a fan of Chukka boots. The desert boot’s close cousin, Chukka boots are essentially a beefed-up version of their relative. While the basic outline remains the same, Chukkas have a slightly more streamlined silhouette and are made of sturdier leathers and more durable rubber soles. All around, the Chukka is a brawnier, sleeker version of the desert boot.
The Chukka boot’s pedigree, like so many garments in the traditionalist’s wardrobe, comes from sporting lore. More specifically, a period of play during a polo match, which is called a chukker. This word is an anglicization of the Hindi word chukkar, which roughly translates to “a turn”. Although Chukka boots themselves were never worn while playing polo, they closely resemble the boots that were worn; it’s also true that they were likely worn by the players after matches.
But enough about the Chukka, this piece is about the desert boot, after all. The more relaxed of the two boots has a decidedly less roundabout history than that of its cousin. While Chukka boots draw their lineage to sport, desert boots can trace their lineage to that other major forerunner of classic clothing: the military.
The desert boot as we currently understand it – soft, ankle-height leather upper with a flexible sole – can be directly traced back to World War II, when an observant British soldier took note of the crepe-soled footwear worn by Burmese troops. This soldier was no typical infantryman, however; his name was Nathan Clark, heir to the legendary English shoemaker C&J Clark, now known as Clarks. Upon returning to Europe, the young Clark had not only a World War victory under his belt, but also the outline for a shoe design that would be entirely new to the Continent and the Western world.
While the history of the desert boot itself is less convoluted than the Chukka’s, the same cannot be said for the history of my relationship with the former. I used to think desert boots could actually ruin an otherwise stylish outfit. So, you’re wondering, how did I get to the point where I’m writing about how much I appreciate them?
The first reason is through simple exposure. The more I have been entrenched in menswear and classic tailoring, the more I have been exposed to a plethora of different styles and, with that, a plethora of different garments. One of those items that kept popping up time and again was the mighty desert boot.
As I saw desert boots mixed into classic menswear ensembles more and more, I realized some of my personal heroes actually wore them frequently. One of my style heroes – Andy Spade – wears them often with a corduroy coat and pink OCBD, creating a rumpled-yet-put-together vibe that has more than a healthy dose of Ivy. Meanwhile, one of my life heroes – Anthony Bourdain – wore them frequently with jeans in a more dressed-down manner. And as the chef-turned-TV-host’s star grew, his footwear of choice became something of a trademark for him.
In fact, Bourdain wrote about the boots in a 2013 Esquire article, saying, “Comfortable shoes are important — I like Clarks desert boots because they go off and on very quickly, they’re super comfortable, you can beat the hell out of them, and they’re cheap.” Comfort, durability, and value: all true Ivy virtues.
As I analyzed how these heroes of mine wore their desert boots, I came to see how they could fit into my own wardrobe. Which leads me to the second reason I have adopted this venerable item into my rotation: I bought a pair. A pretty good pair, too; mid-2000’s J. Crew, 100% suede upper, made in Italy.
No longer was the concept of how they could fit into my own wardrobe just an abstract notion, but now I actually had the materials to pull the experiment off. My first attempt at mixing them in is pictured below. They are featured in a transitional outfit marking the end of summer and the beginning of fall. Hacking jacket, patchwork madras button-down, jeans, and discreet leather belt. As you can see, I have no fear of mixing and matching!
Since I’ve had these boots for just a few weeks now, I have only had the chance to wear them once or twice beyond the walls of my house. However, with true autumnal weather fast approaching, I’m excited to emulate Spade and Bourdain and mix these tried-and-true footwear classics into my everyday rotation.
- Trevor Jones