On days when comfort is prized, choose a beige crew-neck sweater and tobacco chinos. Bring an added dose of polish to this ensemble by wearing a pair of dark brown leather chelsea boots. In the winter season, when practicality is prized, it can be easy to surrender to a less-than-stylish look. But this look is a striking illustration that you totally can stay comfortable and remain equally stylish in the winter season. An ensemble like this will help any 40-year-old gentleman outshine his peers.