Marry a suit with a navy overcoat to exude elegance and polish. Introduce a pair of brogues to the mix to make a classic outfit feel suddenly fresh. During the winter months, when warmth is crucial, it can be easy to surrender to a less-than-stylish outfit in the name of convenience. This outfit, however, is hard proof that you can actually stay comfortable and remain stylish at the same time in the winter months. Dressed like this, any over-50 man will put the younger generation to shame.