Putting together a grey three piece suit and a white and black check dress shirt will be solid proof of your outfit coordination expertise. To give your ensemble a more laid-back feel, complement this outfit with dark brown leather derby shoes. If it's one of those dreary fall afternoons, what better to cheer it up than a on-trend outfit like this one? So if you're looking for dressing tips for gents in their sixties, this combo is a good example.