Wear a dress shirt with beige dress pants if you're aiming for a clean-cut, stylish look. Bring a dressed-down twist to this outfit with black leather derby shoes. During winter, when practicality is imperative, it can be easy to settle for a less-than-stylish ensemble. However, this ensemble proves that you totally can stay snug and remain stylish in winter. As a middle-aged guy, you're guaranteed to appreciate this look.