A white dress shirt and charcoal wool dress pants are among the fundamental elements of an elegant man's wardrobe. To introduce a carefree feel to this outfit, add a pair of tobacco leather brogues to this outfit. As you can see, it's super easy to look seriously stylish and stay comfortable come chillier weather, all thanks to combos like this one. Overall, a foolproof choice when it comes to style for 50-something gentlemen.