Chukka boots or Desert Boots are rather popular today, and there are many manufacturers of casual chukka boots and also bespoke versions of it. Considering the casual nature of the Chukka boot, I would never combine a crepe sole Chukka boot with dress pants or a suit.
At the same time, an elegant Chukka boot can be paired like a suede shoe, and looks great with dress pants and suits. For example, I have an elegant pair of St. Crispin Chukka boots in mid brown suede leather that goes very with almost anything I wear.
The possibilities of incorporating them into one’s wardrobe are endless. Dress Chukka boots with thin leather soles on an elegant last in brown can be paired with a navy or mid-gray suits and a range of other colors and patterns.