For relaxed dressing with a city style take, wear an olive parka with jeans. Introduce a pair of black and orange athletic shoes to the mix to make a dressy outfit feel suddenly edgier. Figuring out a well-coordinated ensemble can be a bit of a juggling act on its own. Add cold temps into the equation, and the whole thing becomes even more difficult. Don't despair, this here is your winter fashion inspo. This getup is a good illustration middle-aged guys can still very well draw compliments.