Go for elegant men's style in a grey suit and a white and black vertical striped dress shirt. Complement this outfit with dark brown leather brogue boots to make a sober look feel suddenly fresh. Putting together a pulled together combo can be challenging on its own. Enter below-freezing temps into the equation, and the whole thing becomes all the more difficult. Fear not, this here is your winter inspo. Classy getups for stylish 20-somethings aren't actually that hard.