This casual combo of a black and white horizontal striped henley shirt and navy jeans can take on different moods according to the way it's styled. Puzzled as to how to finish this ensemble? Round off with dark brown leather casual boots to turn up the classy factor. On not-so-bone-chilling afternoons, you can work this easy-to-transition outfit and look absolutely awesome. This outfit shows how to keep succeeding in the casual fashion department as a guy in his thirties.