Is crossdressing flattering to women?

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.


5 comments on “Is crossdressing flattering to women?

  1. Vivienne says:

    Hi Thorin,

    I actually quite agree with most of what you say, though I am not sure your examples are particularly well-chosen.

    I can completely see why some women find crossdressing distasteful and uncomfortable. I think that boils down to three things, and some of them pertain to men too!

    First, while some crossdressers are beautiful, the best that some can manage is a parody of femininity. Secondly, I think that for some of them, the obvious pretence of someone trying to be something they are not is very uncomfortable for some observers; it’s the “uncanny valley”.

    Third, I don’t believe that crossdressing is driven by innate femininity, and therefore I think (for most crossdressers) their motivations and feelings are not the same as those of women. I think it’s desirable for some crossdressers to insist that they are just like women, but I don’t think this is true in the majority of cases. It comes back to Helen Boyd’s observation: crossdressers don’t want to be like women; they want to be like men think women are.

    All of that said, there are exceptions all over the place. For myself, I loathe pretence and sham, yet I enjoy crossdressing. How do I resolve this? It may sound like a semantic fudge, but I don’t consider myself to be a woman, just a man who enjoys wearing women’s clothing.



  2. thorin25 says:

    That’s why I like you Vivienne, you are honest about what you do, rather than saying, “my crossdressing is good because it flatters and compliments women.” I appreciate how you own up to your actions and look at them honestly. Although we disagree about crossdressing, at least we can agree about some of the stupid rationalizations we as crossdressers sometimes like to tell ourselves.

    I’d be interested to hear more about my examples being not well-chosen. I’d like to correct them and make them better if you point out the problem.


  3. Vivienne says:

    Hi Thorin,

    I’m glad you appreciate my honesty.

    I think you should steer away from race to make your point. I don’t know any examples of white people who try to make themselves look like black people. As for India, the caste system has been in place for centuries, where it is considered desirable to have pale skin (which implies you don’t have to work out in the sun but are wealthy enough to sit indoors). When Indian women attempt to bleach their skin, it isn’t in mimicry of a Western ideal of beauty, but instead using modern techniques to improve their chances of marrying a suitable partner.

    I think there is a tendency for people in Western countries to identify with all sorts of tribal cultures around the world. I think that’s because some people consider tribal cultures to be more harmonious with nature, or spiritually aware, than our modern materialistic one. For most, it’s nothing more than wearing a shark tooth pendant or getting a swirly tattoo. Some people seem to need to take it further, but I think they are few, and I don’t think it’s limited to Native Americans.



  4. thorin25 says:

    I don’t know of many white people trying to imitate black people either. That’s the point. It is strange and offensive not flattering. I understand your point about Indians dying their skin. I’ll edit my post and take out that example. I guess I didn’t fully understand why they were doing what they did. I’m glad to be corrected. Thank you


  5. Andrew says:

    In my humble opinion I have found very very few women that look at cross dressing as flattering or even acceptable. Most women who are married to a CD are not happy or are flattered by their husbands wearing women’s clothing. I have heard and seen words like perverted, wrong, disgusting or even sick yet in this post modern world we live in everything must be accepted or else. Vivienne, I also appreciate your comments here even if you don’t agree with all views shared.
    When I was out there I had many women complement me on my taste in clothes and we had fun conversations where I was told I was so brave for doing what I was doing and being so transparent. Most however supported me more out of the relationship we had rather than being honest with me that they didn’t get it and were confused. Women that accept men who present as “sissies” are looking to dominate and use that man. The truth is that if women were to be totally honest the whole idea of a man in female garb is repulsive to them so how could we ever think that we are flattering to women. Relationships are at best hurt by it and at worst destroyed by it. Just my humble opinion based on my life experience.


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