This combo of a sweatshirt and black chinos makes for the perfect base for a casual and cool ensemble. Black athletic shoes will give a dash of stylish effortlessness to an otherwise mostly dressed-up look. In the winter months, when functionality is everything, it can be easy to settle for a less-than-stylish look in the name of functionality. However, this look proves that you can actually stay snug and remain stylish during the winter months.