They were my first real deal shoes. I remember my mom buying them at an outlet mall during vacation. In all likelihood, I was wearing a Little League t-shirt and shorts and a Phiten necklace (practically mandatory for Little Leaguers at the time) and a pair of Nike Shocks (oh man, I thought these were sick).
It was BOGO at Clarks.
Little did I know I was stepping into (pun intended) a tradition, stretching back to British soldiers in Africa and polo players in India. The chukka boot became my favorite shoe. I’d iterate over the coming years: black suede, nubuck, chocolate, even some thick gum-sole Wallabees.
Chinos or jeans? Church or school? It didn’t matter. They always worked.
They weren’t tennis shoes. They weren’t cowboy boots. They weren’t “try-hard” dapper. It was a balance of style I’d only recognize later in life, a kind of refined ruggedness. Here’s Steve Macqueen and Daniel Craig rocking cardigans and desert boots. It doesn’t get much cooler.
A few words regarding technical clarity: what’s the difference between a chukka boot and a desert boot?
The former is a broad term for an ankle-high boot with 2-3 eyelets. The origins of the name is a little messy. Some think it derives from the Indian term for a leisurely walk (“chukker”). Others point to the game of polo, which involves a specific period called a “chukka.” These unique boots were popular for British polo players in India. Either association might be correct, though it doesn’t particularly matter.
All that to say, the desert boot is a specific type of chukka boot, one that Nathan Clark discovered British troops wearing in the deserts of Africa. It maintains the basic qualifications of a chukka (e.g. ankle-high, 2-3 eyelets) while also typically requiring a crepe sole and suede leather.
So, all desert boots are chukka boots, but not all chukka boots are desert boots. It’s the same heuristic you hear about bourbon: all bourbon is whiskey, not all whiskey is bourbon.
Although I’ve tried a number of chukkas, I’ve always gravitated toward the desert boot as the ideal. Specifically, I love the cut of Clarks’ original. It is—after all— the original popular version of the shoe. The shape is perfect, not too low or high. It’s not funky or “innovative.”
A pair of Clarks hits me like a golden ratio.
Another king of cool, Anthony Bourdain, was a famous advocate of Clarks. In an interview with Esquire, he remarked:
“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.”
They are truly a powerhouse of value. You can pick up a brand new pair on Ebay for about 40$-50$.
Although I love my Clarks, there’s a problem.

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