Combining a navy long sleeve shirt and black dress pants is a surefire way to inject a sophisticated touch into your closet. Introduce a pair of black leather derby shoes to your outfit and you're all done and looking boss. So as you can see, this ensemble is a really good choice, especially for awkward fall weather, when the temps are falling. If you're wondering what you should wear as a gent in his 40s, this pairing gives a proper idea.