One of the most popular ways for a man to style a hoodie is to pair it with black jeans for a laid-back ensemble. Grey suede desert boots will breathe a sense of refinement into an otherwise mostly dressed-down ensemble. During the winter season, when comfort is critical, it can be easy to surrender to a less-than-stylish ensemble. However, this ensemble is a striking example that you totally can stay cozy and remain stylish at the same time in the winter season. So if you need outfit ideas on how to dress as you move through your teenage years, this ensemble is a great example.