This pairing of an overcoat and brown dress pants is a life saver when you need to look like a British gentleman. Our favorite of a ton of ways to finish this ensemble is with a pair of dark brown leather casual boots. In the winter season, when warmth is the priority, it can be easy to settle for a less-than-stylish outfit. This outfit, however, is hard proof that you can actually stay cozy and remain equally stylish in the winter season. So if you're on the lookout for outfit ideas on what to wear after 50, this getup is a good example.