You'll be surprised at how easy it is for any guy to get dressed this way. Just a white and black turtleneck paired with jeans. Clueless about how to complement your look? Finish off with a pair of dark brown leather casual boots to polish it off. Rest assured, this outfit will keep you comfortable as well as looking sharp in this weird transition weather. If you're wondering what you should wear as a middle-aged guy, this combo gives a proper idea.