Pair a black shearling jacket with black check wool dress pants if you're going for a proper, sharp ensemble. During winter, when functionality is prized, it can be easy to settle for a less-than-stylish outfit in the name of functionality. However, this outfit is a clear example that you totally can stay snug and remain equally stylish during winter. Sartorial inspiration like this will help you remain amazingly stylish at 40 plus.