You'll be amazed at how very easy it is for any man to get dressed this way. Just a dark brown sweatshirt and black cargo pants. When it comes to shoes, go for something on the more elegant end of the spectrum and complete your outfit with chelsea boots. There's no nicer way to brighten up a bleak autumn afternoon than a killer getup like this one. If you're wondering how you should dress as a gentleman over 40, this getup is a good source of inspiration.