For an effortlessly classic ensemble, consider teaming a duffle coat with a navy denim jacket — these two items play really well together. If you don't know how to finish, a pair of black leather casual boots is a wonderful option. In the colder months, when warmth is paramount, it can be easy to settle for a less-than-stylish outfit in the name of practicality. However, this outfit is a practical illustration that you can actually stay warm and remain equally stylish in the colder months. A proper ensemble for any man over 50.