This pairing of a crew-neck sweater and jeans is super easy to replicate and so comfortable to rock as well! Complete this outfit with a pair of black leather casual boots to effortlessly step up the wow factor of your outfit. While it can be tricky to stay on-trend in subzero temperatures, it's getups like this that prove it's actually possible. Perfect if you're hunting for some incredibly inspiring casual style for over-40 guys.