For a fail-safe relaxed casual option, you can never go wrong with this pairing of a brown shearling jacket and charcoal wool chinos. A cool pair of brown leather casual boots ties this outfit together. In winter, when warmth is top priority, it can be easy to surrender to a less-than-stylish outfit in the name of convenience. But this outfit is a striking illustration that you totally can stay snug and remain stylish in winter. A great example for any guy who's figuring out how to dress as a 20-year-old guy.