Some Chukka boots can get used in casual or formal style applications, while others are strictly casual.
Rubber sole versions always get worn casually. It is best to wear them with jeans or khaki pants. You don’t want to wear them with a suit or dress pants because they do not go together.
Leather soled Chukkas with contrasting stitching is also considered a casual boot. Because of the different colors, they should never get worn with dress pants or suits.
Thin leather-soled boots in a dark brown or tan colors are the most versatile type. They can be dressed up or dressed down depending on the season, event, or your signature style. You can pair these with a suit, Chinos, dress pants, khakis, jeans, or even shorts.
In my opinion, the best Chukka boots for men are the classic brown suede boots with a thin leather sole. These are unquestionably my favorite type of Chukkas. Choosing those gives you the ability to wear them year-round, with virtually any outfit. Not to mention how much easier it is to put your outfits together in the mornings.