Show that you know a thing or two about men's fashion in a white and navy vertical striped dress shirt and charcoal skinny jeans. Take your ensemble down a dressier path by wearing a pair of black suede tassel loafers. This combo isn't a hard one to score and it's summer-friendly, which is most important when it's extremely hot outside. A practical illustration for any gentleman who wonders how to dress as a guy over 50.