A blue crew-neck sweater and dark brown chinos worn together are a savvy match. Finish this getup with tassel loafers to serve a little mix-and-match magic. In the winter season, when functionality is above all, it can be easy to settle for a less-than-stylish getup. However, this getup is a striking example that you can actually stay warm and remain equally stylish in the winter season. This outfit is something men in their forties can wear with confidence.