I think this has been a really interesting thread.
I wouldn't complain or make the person feel awkward if a cross-dressing male was on a hen night with me. I hadn't really thought about the issues that deeply. My DP finds men dressing as women (Mrs Brown, drag in general) as very icky, but has no problem with men either behaving in non-macho fashion or for example, having long hair.
Rachel/Richard I'm pretty sure is probably going to carry on in the women as 'lambrini advert' bubble but its definitely made me (and a few others I'm sure) think a bit differently.
My own tuppence about issues I have, as a feminist I had struggled for years with the whole make-up thing and why women feel the need to wear it, high heels also. I had felt it was very un-feminist to wear make-up.
However, recently I have got into rock music again, was into it pre-DC and find it interesting that quite often male rock musicians dress in a 'feminine' style clothes although being very clearly hetero males, they aren't pretending to be women, they just like and think they look good with long hair & make-up.
I think guys can look fab with make-up/long hair and it is unfortunate that they are called 'gay' or 'fags' for doing so. Women can have a lot more freedom in terms of dress/appearance than men imo. We can in most places wear trousers or skirts. Although some places are still very behind (schools that require girls to wear skirts, jobs that require women to wear make up/dresses, am thinking 'air hostess'.
I wear make-up now if I feel like it.