As you can see here, looking casually neat doesn't take that much effort. Just make a navy shirt jacket and a grey sweatshirt your outfit choice and be sure you'll look incredibly stylish. On the fence about how to finish your ensemble? Finish with brown leather derby shoes to step up the wow factor. This ensemble is our idea of perfection for when temps are dropping and autumn is settling in. This outfit is a clear example gents over 50 can still very well draw compliments.