For a casual and cool getup, consider teaming a navy denim jacket with a beige crew-neck sweater — these two items work really great together. Want to go all out on the shoe front? Introduce black leather derby shoes to this outfit. When it comes to dressing for fall, nothing beats a cool ensemble that will keep you snug and looking your best. And if we're talking style tips for 50-something guys, this outfit looks great on almost any man.