The origin story of the chukka boot is shrouded in equal parts of history and mystery.
A common, but unlikely assertion is that chukka boots were originally developed for riding horses. The name chukka comes from the sport of polo, where the matches are split into segments of play called “chukkas.” However, you’d be hard pressed to see these on a polo field where thigh-high equestrian boots still dominate and chukka boots don’t offer much protection for your calves. Whatever the logic, the name stuck to describe all boots with a short shaft and a few eyelets.
However, the clearest design story harks back to the British military during World War II. For UK forces stationed in North Africa, regulation army boots were excellent for handling the rigors of combat, but weren’t ideal for the hot, sandy desert environment. As the legend goes, soldiers went shopping in the local bazaars to find low-cut boots in lightweight leathers with thick crepe soles. These ‘desert boots’ were better suited for keeping feet dry and sand out, becoming a special favorite for comfortable off-duty wear, before eventually catching on with civilians after war’s end.
In the 21st century, chukka boots cover a wide spectrum of different styles, ranging from the casual purpose of the original desert boot to polished dress chukkas more at home with a suit.