Like the Chelsea, the chukka is also known for hovering in the ankle area. But the similarities end there. This boot comes with two to three eyelets of lacing and is often outfitted in suede. In the 1940s, chukkas popped up as part of a trend toward casual dressing, and by 1950, the British brand Clarks had invented its iconic desert boots (essentially a chukka with a crepe rubber sole), solidifying the style’s spot in shoe history.
How to wear them: A recent resurgence in popularity has everyone from college kids to soccer dads sporting chukkas. And for good reason: It only takes a solid Oxford shirt and straight-leg jeans with a single cuff that gently covers the boot without breaking (so the pants fall straight over the shoe in a clean line) to do these shoes justice.