It is, unarguably, the most famous of chukka boots. If Nathan Clark (of Clarks’ shoes) hadn’t spotted a preference for this two or three lace hole, thin-soled, unlined, round-toed, ankle-height style of footwear among British army officers serving in Egypt during World War II, perhaps it would never have become a style staple. The chukka boot, after all, represents a rare compromise - between shoe and full-on boot - that actually works, and, what’s more, works well with tailoring and casualwear alike. That took time to be really appreciated: when Clark launched a commercial version back home in 1950, the style was widely rejected, in part because it seemed to fall between two stools. But that, precisely, was its benefit.
The chukka boot did not, however, originate in the middle east. For that we must look further east, to India. Or, at least, that’s how the story goes. Whether ‘chukka’ comes from polo - it’s the term used for each seven minute interval of play - or from ‘chukkar’, an Indian term for a leisurely walk, nobody quite knows. The chukka boot might be said - unconvincingly - to be a similar take on the knee-high style worn by players. On the other hand, in 1924 the Duke of Windsor was reported in the US press to have worn a pair, and he was a polo enthusiast. The truth is that the basic form likely pre-dates both considerably: those British officers in Egypt who favoured the comfort the chukka boot offered over more regulation styles? They’d had them made up in the Cairo’s Old Bazaar, based on a more rough-hewn style that had been worn by traders there for centuries. After all, the style - with its one-piece heel cap and quarters, and unadorned vamp - is simplicity itself.