On days when comfort is critical, this pairing of a black shearling jacket and sweatpants is a winner. For times when this look is too much, tone it down by sporting a pair of navy athletic shoes. In the winter months, when practicality is critical, it can be easy to settle for a less-than-stylish look. This look, however, is a striking example that you totally can stay warm and remain equally stylish in the winter months.