For a look that offers functionality and dapperness, consider teaming a polo with black jeans. You can get a little creative with shoes and polish up your ensemble by wearing a pair of brown suede brogue boots. In the winter season, when functionality is imperative, it can be easy to surrender to a less-than-stylish look in the name of practicality. However, this look is a striking example that you totally can stay comfortable and remain stylish at the same time during the winter season.