This elegant pairing of a black waistcoat and navy jeans is undoubtedly a statement-maker. Why not take a more laid-back approach with footwear and complete this ensemble with a pair of dark brown leather desert boots? This combo is basically a staple if you want to stay snug this winter and look equally stylish. If you're wondering how you should dress as a gent in his 50s, this ensemble is a good source of inspiration.