For a never-failing laid-back option, you can't go wrong with this combination of a navy denim jacket and navy jeans. To give your overall look a more elegant touch, complete your outfit with dark brown leather casual boots. During the winter season, when practicality is a must, it can be easy to settle for a less-than-stylish ensemble. This ensemble, however, is a bright example that you totally can stay snug and remain equally stylish in the winter season. Guys wondering how to stay fashionable as you move into your 40s, you have your answer.