There is no easy answer to this question as every woman is different and they have different things they appreciate or dislike.
But I ask this question because I have often heard crossdressers say that their crossdressing should be the highest form of compliment to women. It should show that they value women so much, that they try to imitate them. I guess the way to put this into the best light would be to think of a child imitating a parent because they are modeling after them.
However, I think it’s fairly obvious that most women do not find this activity flattering at all. There are a few marriages out there where crossdressing is tolerated, and a few in which the wife even participates. But for the most part, from what I have read, wives find crossdressing very disturbing and they dislike it to the point of having the marriage end. They do not find it flattering.
Why do they not? I want to answer by stating some analogies that I hope will help to illustrate why they do not find it flattering. Is it flattering when white people try to make themselves look like black people? No. This is offensive in our culture. Is it flattering for Americans to try to pretend they are traditional Native Americans, complete with feathers? No. It is offensive. A man imitating a voice that people perceive as the “traditional gay way of speaking” is not funny, not flattering, but offensive.
Imitation is flattering when the person imitating you enhances their own person-hood and identity by doing so. A violinist imitating and learning from a more skilled violinist, that is flattering. A daughter imitating her mother, that is flattering. A girl at Halloween dressing up like a doctor, that could potentially be flattering to a doctor, knowing that the girl might enjoy becoming a doctor in the future.
Imitation is not flattering when the person imitating you is denying their own identity rather than enhancing it, by trying to take on a new identity that does not belong to them. It is a complicated thing for an American to be attracted to Native American culture. A person might find elements of the culture attractive, but to pretend that they are a Native American themselves and totally take on that culture, could be very unfitting and disturbing to Native Americans. That is a culture and heritage that does not belong to that person. They do not know what it is like to have grown up experiencing the racism this community has experienced. They do not have the years of hurt from past crimes against the Native community, that a true Native American would have. They are not truly a part of that rich cultural tradition, but at most, merely a guest into it. A white person trying to imitate a black person is just offensive. That is an identity that does not belong to them. They are not enhancing their own identity through the imitation, but denying their true identity.
And for a last example. If a woman tried to dress and appear exactly as a man, would men take this as flattery? Some crossdressers might argue that they would but I think for the vast majority of men out there they would not see this as flattery. They would see this as confusion. It would seem that the woman is confused, thinking that men are better than women, so she is denying her identity as a woman and trying to appear as a man.
So I do not believe crossdressing is flattering to women. I think it is a very foolish rationalization to try to help crossdressers feel less guilty about what they are doing when deep down they know the activity is wrong and messed up.
Thoughts? Feel free to challenge me on this. I’m open to correction, but this is how I see it for now.