Nail casual menswear in a brown shearling jacket and charcoal chinos. Brown leather casual boots are a nice choice to round off your ensemble. In the winter season, when warmth is prized, it can be easy to surrender to a less-than-stylish outfit. However, this outfit is hard proof that you can actually stay comfortable and remain stylish at the same time during the winter season. A wonderful example of how to dress fashionably as you drift through your 20s.