Extra dapper and functional, this casual combination of a black shearling jacket and sweatpants provides with variety. Shake up this getup with more relaxed footwear, such as this pair of white and navy athletic shoes. In the winter season, when practicality is paramount, it can be easy to settle for a less-than-stylish ensemble. However, this ensemble is a striking illustration that you can actually stay comfy and remain stylish at the same time in the winter season. Those who wonder how to wear modern off-duty outfits as you progress through your teen years, you have your answer.