If it's ease and functionality that you're seeking in an ensemble, wear a brown bomber jacket and a turtleneck. Finishing with a pair of dark brown leather derby shoes is a fail-safe way to inject a touch of polish into your outfit. When you're having one of those bleak autumn days, sometimes only a neat outfit like this one can brighten things up. Gentlemen who are curious how to dress well as you age into your 40s, you have your answer.