A man should have a minimum of four dress shirts for work. This allows him to rotate his shirts so that they always look fresh. It also gives him a backup in case one of his shirts gets stained or wrinkled. A man who has more than four dress shirts is generally considered to be well-dressed. However, it is not necessary to have a large wardrobe in order to be fashionable. As long as a man's shirts are well-tailored and fit well, he can get by with a small number of shirts.