As you can see here, it doesn't require that much effort for a man to look casually classic. Just make a shirt jacket and a white dress shirt your outfit choice and be sure you'll look amazing. Finishing with a pair of brown leather derby shoes is a simple way to bring a bit of flair to this outfit. As you can see here, this ensemble is a really wonderful option, especially for awkward transition weather, when the temps are starting to drop. This getup is probably exactly what you've been looking for as a guy over 50.