Wear a blazer with navy wool dress pants for extra smart attire. The whole look comes together quite nicely when you complement your outfit with a pair of brown loafers. During the winter months, when practicality is critical, it can be easy to surrender to a less-than-stylish ensemble in the name of functionality. This ensemble, however, is a striking illustration that you totally can stay snug and remain stylish at the same time in the winter months. A proper combo for any over-40 man.