Pairing an overcoat and charcoal herringbone wool dress pants is a surefire way to inject your styling routine with some masculine elegance. If not sure about what to wear in the shoe department, go with a pair of brown dress boots. In the winter season, when practicality is key, it can be easy to surrender to a less-than-stylish outfit. This outfit, however, is hard proof that you totally can stay cozy and remain stylish at the same time during the winter season. Style like this is what will earn you respect from your peers over time.