This refined pairing of a navy waistcoat and charcoal dress pants is a popular choice among the sartorially superior chaps. Complete this look with a pair of casual boots to bring a hint of stylish effortlessness to this ensemble. During the winter season, when comfort is above all, it can be easy to settle for a less-than-stylish look. But this look is a striking example that you can actually stay warm and remain equally stylish during the winter season. The ability to rock combinations like this is one of the benefits of reaching middle age.