A blue suit and a crew-neck t-shirt are among those sport-anywhere-anytime items that have become the key elements in any modern gent's collection. Want to play it up on the shoe front? Complement this ensemble with black leather derby shoes. This combination is a viable choice when it comes to figuring out a kick-ass look for awkward fall weather. If you're not sure how to dress your age while looking fashionable, this combo is a practical example.