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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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.
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Lynn Jones
Lynn Jones
15 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 😀

Vanessa Law
Vanessa Law
15 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…

Diana Kay
Diana Kay
15 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

Cassie Humes
6 years ago

I would love to have a lot more outfits band heels I love being dressed this way it so had to take off I hope u all can help me find beautiful and sexy things to ware thanks

Sultanna Goodfoot
3 years ago

I’m a Straight Male Women’s Shoe Fetishist Crossdresser of Women’s Footwear especially High Heels. I so much wish I had the courage to just be Myself Totally, to the whole World. I only exposed my secret closeted lifestyle to certain areas and certain people who are not judgemental or negative. I was told that if I am ashamed of something, I should not do it. In my older years of age, I am not as of yet, totally out. Unless I get intoxicated & say F*** it, which I do periodically.

Sultanna Goodfoot
3 years ago

I wish that Shoes and Clothing, etc. were just that. Not Male or Female. But then, the power to wear Women’s Footwear or whatever, would take away our expression of. being different from what the Norm dictates that we have to be.

Last edited 3 years ago by Sultanna Goodfoot
Falecia McGuire
Active Member
2 years ago

I’m virtually certain that I will or would continue to or increase my crossdressing if it becomes more acceptable. The “forbidden aspect” is not the attraction for me. I just love the look of womenswear and the feminine form. When I get lazy, I let my weight and fitness slide. But the more I’m able to dress, the better my discipline, because a slender waist above my hips is a significant part of the allure for me. I also love wearing high heels of any sort. I’m amazed at the number of women who miss the opportunity to wear heels.… Read more »

Sarah Kanter
Trusted Member
2 years ago

I think it wouldn’t be near as much fun if it was normal. I mean, if all the guys in my office regularly wore skirts, dresses, etc. then it wouldn’t be much fun to do it. The fact that it is deviant is part of the fun. I don’t want people to think I’m a pervert and dangerous to their children, or mentlally ill or have abandoned my faith (or any other stigma that you can imagine), but I don’t mind if they think I’m weird or laugh a bit.

Trusted Member
2 years ago

I wish for that day to come in my lifetime, while I have years to enjoy it. To me, crossdressing and appreciating feminine fashion by wearing it will always be unique because it makes me feel something. If crossdressing were more acceptable, I would purge a lot of my male wardrobe, but still keep some male things I adore…like suits, sweaters, dress shirts. It would be so nice to have more clothing options. And I would gladly wear women’s fashions that are a few years old because I’m a thrift store hunny. There are some tasteful fashion photos if you… Read more »

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