Master off-duty menswear in a navy denim jacket and dark brown chinos. Black leather casual boots are a fail-safe way to bring an added touch of style to this outfit. In the winter season, when functionality is a must, it can be easy to surrender to a less-than-stylish ensemble. This ensemble, however, is a striking example that you can actually stay cozy and remain equally stylish in the winter season. Wondering what you should wear as you reach your 50s? This getup is the perfect answer.