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
A great article Mr. Jones. I like how you pulled your heroes into it. Maybe I am missing something — I don’t see your first attempt photo, and I would like to.
Has anyone had experience resoling crepe shoes?
Fixed – JB
@Grant, thank you very much!
Noticed the same about the photo — just emailed JB about it.
No experience in resoling crepe-soled shoes as I’m still very much a novice with this type of shoe.
Fixed – JB
I wore them during high school back in the mid to late 60″s. The high top kept catching the trouser bottom, which I intensely disliked so I eventually migrated to the lower version which I liked a lot better and has not been made in years. I stopped wearing them when the low version was discontinued.
What about trying them with khaki shorts? You know, go all-in, ‘Montgomery of Alamein’?
I actually love the look of desert boots, but my personal experience with them has been someone tainted by the LL Bean pair I bought on a whim: they’re minimally constructed and have little structure and support, which is fine; but my pair actually had seams and joints at the sole which dug into my feet & ankles, making them unwearable.
Maybe I need to try again by upgrading to Clark’s?
I last wore desert boots in junior highschool (1969). Then Frye Boots became the rage and DB’s seemed to fade into the past. I recently have been viewing Drake’s version of the desert boot and might just buy a pair.
Andy Spade hosts a Celebrity Shopping piece at New York Mag’s The Strategist. First on his list — Desert Boots! He rolls a cuff in his pants. It’s a good look; shows those boots off.
Can someone link to the Clark’s Mr. Bourdain is wearing? Is it classic Clark’s version in gray suede? Link here: https://www.clarksusa.com/c/Desert-Boot/p/26161792
I appreciate this post, Mr. Jones. I used to wear Clarks desert boots quite often. They’re plenty comfortable unless you’re taking an exceptionally long walk. The only reason I prefer more polished chukka boots nowadays is that I find them a little more versatile: They’ll go with most everything in my fall/winter wardrobe, including suits. (Of course, it could be argued that the desert boots would go with same.)
Grant, your question about resoling Clarks brought to mind a blog I happened upon years ago when I had the same question. Somehow I remembered it, and just managed to find the link (which I hope is OK to post here — if not, sorry for the trouble of deleting it).
Thank you Nevada — very thoughtful of you. I am looking at your link now. I have a pair of Allen Edmonds Southsides. They are blucher desert shoes; blucher tops with crape soles. They are dirt cheep on ebay. Now I am thinking of some desert boots.
I’ve got three pairs of desert boots: classic sand, medium brown and blue camo (don’t ask). Running shoes had been my default casual shoes for more than 40 years. A couple of years ago, I stumbled onto Ivy-Style and upgraded my jeans to khakis, and my New Balance to Clarks. The rest is history in the making.
I have two pair (both Clark’s). I wear the original softer one around the house with old khakis and wear a pair of Bushacre 2 in beeswax with 5-pocket pants. I can’t wait for the temps to drop enough here to pull them back out.
hey what happened to you IG? you stopped posting pics…just wondering.
I have a pair of Clark’s desert boots and, as have others above, find them very comfortable. My only complaint is the high top of the boot gets caught on the cuff of my pants and looks terrible. Perhaps I should cuff my pants . . . .
@Jericho, thanks for inquiring. I wasn’t aware you were a follower.
That account was created entirely for the purposes of further exploring menswear. Learning, connecting, and sharing. I had it up for over a year and it accomplished all of those things, for which I am very grateful. However, as my profile grew, I faced two issues. First, it was simply a lot to keep up. Secondly, I was seeing a lot of negativity (not necessarily directed at me, just in the online world in general). Given that I had created it for in order to get my mind off all the crazy things going on in the real world (the pandemic, finishing my master’s, work, etc.) — as a form of enjoyment — and it no longer became enjoyable, I decided it was a good time to shut things down. Of course, that in no way means clothes still aren’t a really important part of my life, just that I’m not saring WIWT on instagram anymore.
Didn’t desert boots have a moment in the late 60s and early 70s? Or am I imagining things again?
yup i did follow you in IG…am using the handle PINOYPREP….just wanted to say that i enjoyed your posts in IG up until you decided to shut it down.
I have three pairs of chukka/desert boots: Clark’s, PRL, and Loake.
The Loake cuhkkas, in chocolate brown suede, have a beautiful, svelte shape and Dainite soles. Three pairs of eyeholes. Extremely versatile and comfortable, but the Dainite soles are surprisingly heavy.
My Polo Ralph Lauren chukkas? desert boots? are in black suede, with red rubber soles. Three pairs of eyeholes. While comfy, the red rubber makes them stand out more than I prefer.
The Clark’s desert boots are in sand suede, with authentic gum soles. Two pairs of eyeholes make them less comfortable than the others—they feel like they’re not quite securely attached. While easy on the feet & ankles, they are less comfortable for walking long distances in. I won’t get another pair of Clark’s, but I do want another pair of chukkas in sand suede.
I’ve worn “desert” boots since high school (68-73) starting with Clark’s. Now I wear chukka boots by Brooks which work very well. They are a fine edition to any man’s wardrobe.