
Let’s not beat around the bush — both crossdressing and transition take immense amounts of courage. While some may argue that they are different types of courage, I contend that being yourself always demonstrates a high level of bravery.
Just for fun, let’s consider something. Namely, “half cross-dressing” or “gender bending” meaning not presenting as one gender or the other, but rather something in between. Not that I’m trying to create more labels in an already label-saturated community, I just couldn’t think of another way to call it.
Does “dressing in the middle” take more courage?
For many of us, the prospect of leaving the house dressed in drag can be daunting. As stated above, it takes a lot of courage. However, the act of cross-dressing involves completely immersing yourself in the opposite gender (clothing, movement, attitude). There is still a certain level of normalcy (as defined by society) in this.
Even for those of us who do not pass, people can see that we are presenting as female (or male for FTMs). But what about those in our community that choose to blur lines rather than cross them?
I’m talking about the dresser that wears a man’s shirt, man’s shoes and man’s underwear with a flowing skirt. Or perhaps you’ve seen a guy wearing a dress with matching accessories, even carrying a purse but with no wig or makeup.
They call it many things, but at its heart it is still cross-dressing and in my opinion it takes even more bravery to dress this way and hold your head high. To me, it’s like the ultimate middle finger to society’s gender constraints.
In essence, you are saying “I want to wear something that was made for women because I like it, it feels good, it’s pretty, etc. but I’m not presenting as a woman.” I really admire those in our community that do things like this. Personally, I don’t think I could ever do it on my own.
Honestly, this is only a topic you would see discussed on a website like this. Part of me wanted to show my support and admiration for our brothers and sisters that toe that line and part of me just wanted to ponder a lighthearted question.
What do you think?

{ 11 comments… read them below or add one }
I don’t know. Being “half-dressed” you’re clearly making no bones about what you’re doing: here I am, a man, wearing a skirt (or whatever). But this isn’t necessarily more risky – since, by not attempting to pass in the slightest, you’re already demonstrating that you have the confidence to do this and not give a toss (or at least you’re fronting that attitude, even if you don’t necessarily feel it). So, whether it takes more courage… I guess that depends on what you’re afraid of. If you’re afraid of being outed then, yes, it probably would be quite brave
just saw this: http://hisblackdress.blogspot.com/
and thought of this post!
i think this dude is being quite brave and really creative and awesome too!
I think the whole idea of half-crossdressing is stupid!
Let’s get this right, for a men to wear a skirt, or nlyons and high heels is cross-dressing. But I got to say, it still, I girl can wear men-style pants, shirt and shoes and call it style of today. Or they the right to choice what clothes they wish to wear. And a men wants to wear a skirts, etc, etc. And it’s crossdress still. I don’t know what standard. It’s base on . But if you go back far anuff you’ll find the styles of men differ from the 20th-21-centary . I want change! DO YOU!
As someone who goes out as a guy in skirts a lot more often than he goes out en femme, I don’t really think it is any braver for me to do so except possibly with the caveat of there being zero-anonymity because it’s my 100% recognizable male face out there in the open if someone who sees me were to cross my path, but then again I’m very open about the fact that I crossdress so it doesn’t bother me to get recognized. I think dressing as a man in gender bending clothing has risks, but so does presenting as a woman, so it’s all a wash in the end and we all should be supportive of each other to work towards the same goal of more universal acceptance in the end.
And to Warren, thanks for calling my personal sense of style stupid, glad you’re open minded to people’s choices. As to Andrew, yeah it’s silly that a guy in a skirt is crossdressing and a woman in pants aren’t. However, I find that rather than squabble over terms, I get a lot more acceptance for how I dress when I just carry myself with poise and confidence in the things I want to wear.
I like reply on that Rye. Where I live. Then don’t. It you have be normal. Second I personally have not it seen this in public of course!I like your train of thought. There this site I accidently discovered called andrognbeauty.com I think. But you find it on a site called femulate.org. The it’s about this male dresses androgusly. I think you might like it!
If I was brave enough to I’d go half dressed. The few times I have at clubs it felt more comfortable than full dressed. I may not always want to be a man but long ago I discovered I didn’t want to be a woman, I sometimes feel I fall between the lines and wish gender had more options.
I sometimes also get the feel that if your just a male crossdresser, trying to pass like a transsexual is lying. After all I am no woman on the inside and do not want to be one, why would I lie?
I think it takes less courage. Before cross-dressing I would wear articles of women’s clothing without fear because it would either be comfortable or needed for some reason. It’s way scarier to fully cross-dress.
I say it takes the same amount of couraged if the person crossdressed is unpassing, but less if the crossdressed person is passing. A passing crossdressed person will be impossible to find unless somehow undressed which is unlikely in public.
I find it way scarier to half-crossdress, in fact I’m uncomfortable doing it. I don’t know whether that’s because it’s not “my thing”, or I’m just not there yet. Getting comfy enough with yourself to do these things can take a long time.
I think that it takes more courage to wear a skirt as a man in public than it does to go out en femme. En femme means that you are trying to dress as close to a female as possible so it is unlikely that you would be seen as a man wearing a skirt but as a woman wearing a skirt, unless someone discovered the secret. If you are like me and go out wearing a skirt and not dressed as a female and instead easily identifiable as a man, you are more subject to ridicule from people because you are a man wearing a skirt.
I agree with Jessica and do think that it takes much more courage to wear a man’s wardrobe and include a skirt.