This ensemble with an olive wool blazer and a white gingham dress shirt isn't a hard one to pull off and is open to more experimentation. If in doubt about what to wear when it comes to shoes, stick to a pair of brown leather brogues. In winter, when warmth is imperative, it can be easy to settle for a less-than-stylish look. But this look is hard proof that you totally can stay toasty and remain stylish at the same time in winter.