If you want to go about your day with confidence in your outfit, pair a beige shirt jacket with a white crew-neck t-shirt. For something more on the cool and laid-back side to complete your outfit, introduce a pair of brown athletic shoes to the mix. A stylish summer-to-fall transition getup like this one makes it super easy to welcome the new season. This combo is a vivid example middle-aged gentlemen can very well slay in the fashion department.