A hoodie and a mint long sleeve shirt are a great combination to keep in your off-duty rotation. And if you wish to easily dress down this getup with one single item, complement your outfit with a pair of grey athletic shoes. As you can see here, it's super easy to look amazing and stay comfortable when cooler weather comes, thanks to this look. Guys who are curious how to dress fashionably as you move into your 40s, you have your answer.