We love how this combo of a burgundy plaid long sleeve shirt and black dress pants immediately makes a man look elegant and stylish. If you need to effortlessly dress down this outfit with shoes, why not add dark brown leather casual boots to the equation? When you have one of those dreary fall days, sometimes only a neat outfit like this one can get you to face the outside world. Overall, a great option when it comes to outfit ideas for guys over 40.