For an outfit that's pared-down but can be worn in a variety of different ways, marry a short sleeve shirt with a white and black crew-neck t-shirt. Let your sartorial chops truly shine by finishing this look with burgundy leather derby shoes. Loving how this ensemble gets you excited for the fall season in next to no time. This pairing illustrates that figuring out how to dress stylishly over 40 is easier than one might think.