A modern guy's classy collection should always include such wardrobe heroes as a white long sleeve shirt and charcoal dress pants. Dark brown leather desert boots are a surefire way to give a dash of stylish effortlessness to this ensemble. During the winter season, when warmth is the priority, it can be easy to settle for a less-than-stylish look. However, this look is a good illustration that you can actually stay comfortable and remain equally stylish in the winter season. This pairing is hard proof 50-something gentlemen can still very well slay in the style department.