For a look that's absolutely wow-worthy, rock a blazer with blue chinos. Black leather derby shoes are the simplest way to bring a sense of refinement to your ensemble. During the winter season, when comfort is the priority, it can be easy to surrender to a less-than-stylish getup. But this getup is hard proof that you can actually stay comfy and remain stylish at the same time in the winter season. Ideal if you're looking for some amazingly inspiring style for guys in their fifties.