The chukka is an ankle boot with only two or three eyelets. Because of that, they’re typically placed on the more casual end of the boot spectrum and look best paired with either jeans or chinos.
Similar to the desert boot, chukkas come in suede and leather and with a variety of different soles, including crepe, leather or rubber. These are the details that determine the chukka’s “formality tolerance”. A crepe sole would be the most casual, leather most dressy and rubber somewhere in between.
When choosing a chukka for your wardrobe, consider what you need them for and when you’d wear them most. These days, because I don’t wear jeans that often and cotton chinos are my “casual” pants, I prefer something on the dressier side.
The leather chukka is a great choice for everyday wear and easily dresses up your favorite selvedge denim while pairing seamlessly with chinos or even flannel or tweed trousers (though for flannel and tweed, you might do better with a suede pair).