As you can see here, it doesn't require that much effort for a man to look on-trend. Consider wearing a bomber jacket and a black shawl-neck sweater and you'll look awesome. For something more on the classy side to complement this ensemble, complete your outfit with black leather oxford shoes. It's is an exciting pick if you're putting together a knockout ensemble that will take you from summer to fall. This outfit illustrates that dressing your age and looking fashionable are not mutually exclusive things.