Pairing a white dress shirt and charcoal wool dress pants is a fail-safe way to inject your closet with some masculine refinement. Infuse a more laid-back spin into this outfit with dark brown leather derby shoes. During the winter season, when warmth is the priority, it can be easy to surrender to a less-than-stylish look in the name of functionality. However, this look is a bright example that you can actually stay snug and remain equally stylish during the winter season. Overall, a good example of over-50 fashion.