This sophisticated pairing of a white long sleeve shirt and charcoal wool dress pants is a popular choice among the sartorially superior chaps. Our favorite of an infinite number of ways to complement this look is a pair of dark brown leather desert boots. During the winter season, when functionality is a must, it can be easy to settle for a less-than-stylish outfit. However, this outfit is hard proof that you can actually stay comfortable and remain stylish at the same time during the winter season. This combination demonstrates that figuring out fashion as a gent over 50 is not particularly hard.