A dark brown shearling jacket and a turtleneck will add serious style to your current routine. For a more casual take, complement your outfit with brown athletic shoes. In the colder months, when warmth is top priority, it can be easy to settle for a less-than-stylish look in the name of functionality. This look, however, is a good illustration that you can actually stay cozy and remain stylish during the colder months. And if we're talking casual fashion for over-50 guys, this ensemble is ideal.