[WillowTheWhisp]

There are probably many different reasons for the different types of "cross dressing" - pantos for instance. It's the leading young male role which is usually played by a woman. Maybe a woman can look more appealingly boyish and attractive than a man? The female roles in pantos played by men are usually the old or ugly characters such as Cinderella's sisters or elderly widows or wicked stepmothers. This implies that men can look uglier than women. So in pantos it's simply that attractive = female and ugly = male whether the role they are playing is male or female.

As for the likes of Kenny Everitt, he played it so obviously as a man dressed as a woman (beard apparent) that it was done for a joke and never meant to be anything else - in the same way Queen did their "I want to break free" video which was very OTT.

Then you get the likes of Danny LaRue who made a very glamorous woman and maybe for him it was an acting role or an extension of a fantasy but he always insisted that he never wanted to be a woman permanently. All actors play something they are not and he did it brilliantly. He was regarded as family entertainment on such shows as the London Palladium. I remember seeing him as a child and never thought "there's a man dressed as a woman". I don't know what any adult shows were like.

As for Eddie Izzard or Boy George for that matter I think they just enjoy wearing the nail polish and eyeshadow more than anything and there used to be a lot of that about. It's funny where clothing is concerned that no-one bats an eyelid when a woman wears jeans or any other trousers these days or sees a Scotsman in a kilt as perverted but Eddie Izzard in a frock is seen as a freak