For an effortlessly neat outfit, pair a burgundy dress shirt with grey jeans — these items play perfectly well together. Black leather casual boots are the perfect companion to this look. Picking out a standout getup can be a bit difficult at times on its own. Add below-freezing temps into the equation, and the whole thing becomes even more difficult. Don't despair, this here is your wintry outfit inspiration. Those who wonder how to pull off classic and casual outfits as you move through your 20s, this combination should answer your question.