Tap into sharp style in a blue turtleneck and charcoal dress pants. Dark brown leather loafers look wonderful finishing off this outfit. During the winter season, when warmth is everything, it can be easy to settle for a less-than-stylish look in the name of practicality. But this look is hard proof that you can actually stay comfortable and remain stylish during the winter season. No doubt, a smart choice if we're talking dressing ideas for 50-year-old gentlemen.