Rock a blue chambray long sleeve shirt with navy jeans if you wish to look casually dapper without exerting much effort. Hesitant about how to finish off your outfit? Wear dark brown leather casual boots to ramp it up a notch. It's a good choice if you're crafting a well-coordinated ensemble for weird fall weather. This ensemble illustrates that as a 50-year-old man, you still have a wide range of outfit options.