Marry a white dress shirt with charcoal dress pants for ridiculously stylish attire. Add a more casual aesthetic to by rounding off with chelsea boots. During the winter months, when warmth is crucial, it can be easy to surrender to a less-than-stylish outfit in the name of convenience. However, this outfit is a shining example that you totally can stay warm and remain equally stylish during the winter months. A reliable option outfit appropriate for guys in their fifties.