I wear a dress because I want to and love the look and feeling in a dress or skirt. Plus I don't think that for one minute there is anything wrong with a man wearing a dress why should it be frowned upon, we should be allowed to wear what we want when we want without anyone turning their nose up.
We should feel comfortable and relaxed to put on what we want when we want if my wife wants to go out wearing pants with no stares and comments then I should be okay to go out in a skirt.