Socially Acceptable Cross Dressing – will it ever be in style?

Will crossdressing ever be in style

Fashions are a funny thing, and crossdressers are perhaps more beholden to the whims of the fashion fairies than most men. When men dress in women’s clothes, there is something special about looking fabulous and beautiful.

The other day I was thinking – what if crossdressing was normal? You know, if you were just as likely to see a man in high heels and a skirt as a woman wearing a pantsuit. What is there was no masculine gender expression, no feminine gender expression. Would we still be crossdressers? In fact, would we still have the desire to crossdress?

Certainly there must be some part of the transgender experience which is about being unique, in our expression of who we are – the desire to be like woman, yet still knowing that we are a man.

Don’t tell crossdressers they’re normal

If you do, we just might agree. Many organizations, such as Tri-ESS, go to great lengths to remove the stigma from crossdressing. This stigma is entirely a social construct, created by our culture. There are theories as to why crossdressing is taboo – perhaps on a subconscious level it slows down the acquisition of a suitable mate with which to propagate the species?

Nevertheless, fashion will move forward. The brief rise of the metrosexual in the mid 2000’s was a definite step towards a more socially acceptable way for men to express their femininity. Even if all it really meant was that you wore nice clothes and bathed more than once a week.

Socially Acceptable Cross Dressing

I wonder if the next fashion wave will see crossdressing as desirable and trendy? I hope so, but I’m not going to leave my skirt hanging in the closet waiting for it to happen…

P.S. Don’t wait for crossdressing to come in style. Learn how to do your makeup like a professional and look fabulous!

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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
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  1. Lynn Jones 8 years ago

    Metro came and – as you said – went. I think the term popped up in a New York newspaper, although the author said it was over as it began.

    I think we’re seeing a slow rise in male beauty products, but they’re mostly for younger men…. and trannys 🙂

    If the taboo did go away overnight – by whatever means – I personally would rather go all the way. Either be totally male in appearance or present as a female. But maybe I’m just weird 😀

  2. Vanessa Law 8 years ago

    Hehe 🙂
    Sometimes I toy with the idea of going more androgynous – perhaps we’re women’s clothes with a touch of maleness. Perhaps a slightly feminine blouse, foundation, a slight touch of gloss on my lips…

  3. Diana Kay 8 years ago


    I would love it if crossdressing is in style. I love to dress in woman clothes. They are made better, and look better. XOXO

  4. prefab 2 years ago

    I agree, wearing pantyhoes feels great. It’s just a shame it’s not more socially acceptable.

    PS: crossdresser heaven great website. love the topics

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    Vanessa Law 8 years ago

    It’s a good question – why is socially acceptable crossdressing only applicable to women? Some have theorized that the inherent masculine society is more favorable to a woman wanting to “move up” into manhood than a man becoming a “second class citizen” in attempting to be a woman. Personally I struggle to understand this reasoning.

  6. gail 7 years ago

    I’m of two minds about the desirability of socially acceptable cross dressing.
    On one hand more acceptability would cause less stress, and facilitate a more comfortable environment.
    On the other it would reduce one of the thrills, at least for me, namely, the taboo aspect of cross dressing. The sense that one is engaged in something that doesn’t fit neatly into societies pegs.
    I suspect that even if it gains wider acceptance a large enough segment of society would quite vocally frown on “everyday” cross dressing, and would exert enough pressure to restrict the practice. It would be great, however, for public outings to parties, select clubs, and in store shopping at a wider variety of stores.
    So I guess all in all I would welcome a more enlightened attitude
    towards it.
    Possibly, if women continue making economic gains the change will come about sooner than any of us realize.

  7. Dade 8 years ago

    Nothing wrong with this, at all, people should get it more.

  8. Zeljka 8 years ago

    It’s not right that women can dress our man’s clothes any time and any place they like and if I would like to put sometimes pantyhose under my trousers then this is weird or I am a pervert or this kind of things, this is just not right! I like push-up pantyhose which shrink and squeeze, I like that feeling, when they rub against the jeans when put under trousers…why would that be more nasty or something than women wearing a necktie e.g. ??

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