For an off-duty ensemble with a clear fashion twist, you can always rely on a shirt jacket and a grey long sleeve t-shirt. Add a pair of navy athletic shoes to the equation to bring a dash of stylish effortlessness to your outfit. As you can see here, this outfit is a really good option, especially for weird transition weather, when the temperatures are dipping. This outfit demonstrates how to keep slaying in the casual fashion department as an over-40 gent.