For an ensemble that's semi-casual and envy-worthy, opt for a suit and an olive parka. To bring out a polished side of you, introduce derby shoes to this ensemble. In winter, when functionality is a must, it can be easy to surrender to a less-than-stylish outfit. This outfit, however, is a striking illustration that you totally can stay comfy and remain stylish in winter. Guys who wonder how to wear smart style as you work your way through your 20s, you have your answer.