This look with a hoodie and black chinos isn't so hard to pull off and is easy to change throughout the day. Clueless about how to finish off? Introduce white and black athletic shoes to the mix for a more relaxed aesthetic. So as you can see, it's extremely easy to look stylish and stay warm come cooler weather, thanks to this outfit. Think it's hard for 40-something gentlemen to master cool casual style? This pairing is a vivid demonstration of otherwise.