For an outfit that's stylish and camera-worthy, pair a brown gingham blazer with a light blue dress shirt. A pair of olive suede derby shoes adds a sophisticated aesthetic to the getup. Planning a standout getup can be challenging on its own. Enter subzero temperatures into the equation, and the whole thing becomes all the more difficult. Don't despair, this here is your winter outfit inspiration. If you're wondering how you should dress as a 50-something gent, this getup is a good source of inspiration.