Reach for a crew-neck sweater and grey dress pants for a stylish and refined look. A pair of derby shoes integrates nicely within a variety of combinations. During the winter season, when comfort is the priority, it can be easy to surrender to a less-than-stylish look. This look, however, is a good illustration that you totally can stay snug and remain equally stylish in the winter season. This look is ideal for guys in their 50s.