For an outfit that's pared-down but can be flaunted in a ton of different ways, dress in a charcoal wool turtleneck and blue ripped jeans. If you need to instantly smarten up your outfit with one single item, why not complement your outfit with a pair of white canvas low top sneakers? This getup is a nice choice when spring comes. All in all, an ideal demonstration of casual fashion for gentlemen in their fifties.