Go for a casually classic look in a light blue dress shirt and navy chinos. Infuse this look with an extra dose of elegance by rounding off with black leather derby shoes. During the winter season, when warmth is everything, it can be easy to settle for a less-than-stylish ensemble in the name of convenience. But this ensemble is a vivid example that you totally can stay warm and remain stylish at the same time in the winter season. When it comes to fashion tips for 50-year-olds, this combination is ideal.