Extremely stylish and functional, this casual combination of a black shearling jacket and jeans delivers variety. Rounding off with navy and white athletic shoes is the most effective way to inject a more relaxed finish into this look. During the winter season, when comfort is essential, it can be easy to surrender to a less-than-stylish outfit in the name of functionality. However, this outfit proves that you can actually stay warm and remain equally stylish in the winter season. Guys who wonder how to wear modern off-duty style as you move through your 20s, this pairing should answer your question.