For a look that's very simple but can be modified in a multitude of different ways, wear a black crew-neck t-shirt and brown corduroy chinos. Our favorite of a multitude of ways to round off this outfit is with a pair of white and navy athletic shoes. Rest assured, this getup will keep you comfy as well as looking sharp in this in-between weather. Off-duty combinations for stylish middle-aged guys aren't actually that hard, as you can see here.