We love the way this combination of a white and black vertical striped dress shirt and grey dress pants instantly makes a man look polished and dapper. The whole look comes together perfectly when you choose a pair of brown leather loafers. So as you can see, it's a seriously stylish, not to mention spring-appropriate, look to have in your transitional wardrobe. This combo demonstrates that figuring out how to dress well over 50 is not particularly hard.