Dapper up in a charcoal wool blazer and grey wool dress pants. Complete your getup with a pair of brown leather dress boots and the whole look will come together. In the winter season, when functionality is key, it can be easy to settle for a less-than-stylish getup. However, this getup is hard proof that you totally can stay comfy and remain equally stylish in the winter season. A good outfit as you move into your twenties.