"A big part of that popularity is the chukka’s flexibility, both literally and figuratively.
Because they’re lighter and lower than most boots, with a soft, bendy sole material, walking in chukkas is closer to walking in sneakers than it is to walking in Western boots or heavy hiking/expedition boots. A stroll in a good pair of chukkas feels about like it would in Converse All-Stars or something similar, with a little more protection for the feet and ankles from the leather uppers.
The leather material also makes the shoe dressier than a sneaker, but the rubber sole (traditionally in a contrasting color) keeps it informal. The result is a shoe that dresses up casual clothes, and dresses down formal ones."