This pairing of a sweater vest and cargo pants is a safe option when you need to look casually refined in a flash. When it comes to shoes, complete your getup with black leather casual boots. During the winter season, when functionality is critical, it can be easy to settle for a less-than-stylish look in the name of practicality. However, this look is a vivid example that you totally can stay snug and remain stylish during the winter season. Interested in dressing tips for gentlemen in their 50s? This outfit should definitely go to your inspiration folder.