You'll be surprised at how easy it is for any man to get dressed this way. Just a grey plaid blazer and a black turtleneck. To introduce a little zing to this ensemble, complete your getup with a pair of black leather derby shoes. So as you can see, it's extremely easy to look awesome and stay snug come fall, all thanks to outfits like this one. This getup illustrates how to stay stylish as you step into your 40s.