This smart combination of a white dress shirt and a dark brown raincoat is super easy to put together without a second thought, helping you look seriously stylish and prepared for anything without spending a ton of time searching through your wardrobe. Dark brown leather tassel loafers will bring an extra touch of class to an otherwise mostly casual getup. This one is an exciting pick if you're after a knockout summer-to-fall outfit. This pairing is something 50-something gentlemen can wear with confidence.