A light violet dress shirt and grey wool dress pants are absolute mainstays if you're planning a classic closet that matches up to the highest sartorial standards. If you wish to immediately tone down your ensemble with a pair of shoes, complement your outfit with brown leather derby shoes. A killer look that will take you from summer to fall like this one makes it very easy to embrace the new season. This pairing proves that staying fashionable as a guy in his 50s is totally doable.