When is crossdressing not crossdressing?

I saw a post on a crossdressing forum that left me a bit puzzled. The person posting was recounting a recent trip in the vanilla world. They had dressed in ‘women’s clothes’ but these clothes were all so androgynous (jeans, dress shirt etc) that the person said that anyone seeing them may have thought that they were ‘men’s clothes’. I cannot verify this statement as no pictures were published.

This raised some questions, for me, in relation to what is meant by ‘crossdressing’. If you are dressed in such a way that you are not obviously dressed in clothes of the ‘non-conforming gender’ then are you in fact crossdressing, or are you just slightly eccentrically dressed? What is the essence of being ‘crossdressed’ and does it matter?

On a related note, many crossdressers bemoan the fact that ‘women can wear masculine clothes in public with impunity, why can’t we? Why does society judge us for our clothing choices, but not women?’ To my mind this misses the point. Women who wear ‘masculine (or should that be less feminine) clothes are not crossdressing. They are not (at least not in most western societies, anymore) subverting any societal norms and the clothes that they are wearing are still essentially women’s clothes. Jeans and a t shirt may originally have been ‘boys clothes’, but in the vast majority of cases when a women wears jeans and a t shirt, she is wearing a women’s ‘cut’ of these clothes. They are tighter, ‘fancier’ and designed differently to a similar item made for men. These clothes were bought in the women’s section etc and often women wearing these clothes will wear typically feminine accessories (shoes, jewelry, hair etc).

This is a very different proposition for the male to female crossdresser. This person will want to wear quintessentially women’s clothes, bought in a women’s store and matched with women’s shoes, accessories and they will model themselves on women’s features (wigs, make up etc). Very few male to female crossdressers would feel satisfied wearing a kilt and associated ‘traditional Scottish’ apparel. We want to imitate, mimic and otherwise ‘become’ women as much as is possible. Wearing kilts does not achieve this. Indeed a male to female crossdresser may well want to wear a pair of jeans and will wear a pair of women’s jeans, when dressed, in preference to a pair of men’s jeans. Thus the wearing of jeans (arguably a masculine item of clothing) is secondary to the cut and place of purchase of the garment.

I strongly suspect that if a women were to wear a pair of work boots, a pair of men’s denim jeans with a man’s t shirt, cut her hair into a masculine style and generally ‘butch up’ she would probably attract as much attention as the male to female crossdresser does. Society would immediately identify the subverted gender role and get suspicious. The fact is the vast majority of women not wearing skirts and dresses are simply not doing this. They remain squarely in their assigned gender. Of course there are places where this is not true (parts of Africa and the Middle East), but I am confining myself to liberal western states for the sake of argument. I do not think this is unduly reductionist.

Now if we look at the person saying they crossdressed by wearing clothes that were bought in the women’s section, but that were also not obviously (to the casual observer) women’s clothes, was this person in fact crossdressed? I am not clear as to whether the individual was wearing make up, women’s shoes, a wig etc, but I also wonder if this matters. Crossdressing is a very broad church. Not everyone wants to ‘blend’ or ‘pass’. Not everyone dresses in public, some do it purely in private, whether for sexual kicks or not, others take great pleasure in transforming themselves as completely as possible into their concept of the feminine, others want to change their sex. In this context a transexual may consider a transvestite to be a cheap imitation of the ‘real thing’, whilst that same transvestite may look down at the fetishistic crossdresser as some sort of interloper. None of this is helpful.

The point is that we all have different motives for crossdressing and different desired outcomes. A friend summed it up very well when she said that much depends upon who is doing the observing. Some will drive themselves mad trying to figure out what is between the person’s legs, which is none of their business anyway instead of finding out if they are a nice person worth knowing and actually speaking to them as a human being before trying to assign a gender to them. And others will wonder, think ‘interesting’ and then move on to more productive thoughts. Critical to this thinking is that all that matters is what the individual wants to achieve.

It is not up to society (whether broadly, or more narrowly the trans community) to decide what is or is not crossdressing. As long as the individual is happy with the clothes they are wearing then who are we to pass judgement? If you feel crossdressed, if how you are dressed is fulfilling and makes you happy then so be it. It is not up to others in the community to assert hierarchies. Crossdressing is a highly individual activity with nearly as many motives, goals, causes and behaviours as there are people. We have more to gain by standing together in a mutually accepting manner than we have by splintering into different groups. We are so badly misunderstood by broader society that we do not need to add to this confusion by back stabbing, bitching and being divisive. We are all individuals seeking to express something of our innate being and we should support and celebrate each other, our similarities and our differences. I may be naive and an idealist but I would rather see a united trans community than a splintered and divided one.

About the post

crossdressing, femininity, language, transgender


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  1. Brilliant synopsis! The last thing we need are more labels and obfuscation of who we are and what we do. Why is it not simple enough that we exist? Why must additional labels be affixed to us? I simply want to “Be.” I am who I am, and no matter what label someone affixes to me, it will not change.

    I believe, like you, that these labels only seem to splinter us into tribes or niches of sorts. We associate with like minds, we do not expand our boundaries, we do not really combine our efforts to a greater good. I often wonder if it is simply due to these labels that we and others affix to ourselves. Sometimes, we con ourselves into relating and identifying to those labels, because we so oft repeat them. If we repeat it often enough, it becomes our truth.

    Why can we all not identify as transgender, becuase we all fall along that gender spectrum, between one end and the other. I suppose the only real concrete answer is, because so many of us make that part of our identitity. I would not expect a transwoman to continue to identify as a transwoman post surgery, becuase the cruxt of her efforts it to be a woman. By keeping the trans label, she is diminishing her efforts, even if only psychologically, and I can see where such a thing may hold her back. I mean, she would have attained her goal, why be saddled with the obvious baggage that comes with a label? We would all eschew the labels if we could.

    Just my thoughts.

    Ever & Always,
    Caden Lane

    Liked by 2 people

    • Thanks for the comment. Yes, we seem to be on the same page here. The other day I saw someone on Facebook saying that there is ‘no such word as transgender’. She seemed very keen on asserting the superiority of ‘transexuals’ over just about everyone else. I elected not to engage…

      Liked by 1 person

      • In situations like that one it seems they have invested in who and what they are so emotionally, and spent so much time and effort differentiating themselves from the rest of us, that they begin to experience a divisiveness. We begin to fit into this hierarchy where we are essentially an unevolved sub-species. I imagine once she completes her transition, she’d be very quick to shed that transsexual label.

        In the end, we are all human, we all feel and hurt, we all long for more or better, we are fulfilled and yet unfulfilled. The labels serve no purpose other than for somebody else to understand who or “what” we are. The root of most of the labels we have are derived from scientific terminology, a group I cannot fault for having labels. But it should not mean we as laymen subscribe to them, or worse live and die by them. I have no problem acknowledging a transsexual woman’s womanhood. I believe the issue they take with us, is I acknowledge your womanhood. Just as I believe you’d acknowledge mine. They feel we don’t have to pay the dues they pay or endure the things they endure; we can transition back and forth at a whim and continue to embrace male privilege when it’s convenient and suits us and our needs.

        Because of this they feel somehow superior, because they’ve had the fights, they’ve developed the fortitude and they made the full commitment whereas we do not.

        While we have our own struggles and battles, they are not inclined to acknowledge them. I do not begrudge them that. However I do wish we could come together as a community, see things in a similar way; maybe not completely, but acknowledge we are all fighting our own fights and demons, and any help we get from those we should be able to consider peers or big sisters, is nothing but helpful.

        Ever & Always,
        Caden Lane

        Liked by 1 person

  2. Reblogged this on Michelle Has Yet Another Blog and commented:
    I think this post really sums up my feelings. We do spend way too much time over definitions, worrying if we fit into them and being critical of people who do not fit into our definitions. When we really should be spending our time supporting each other to be the person they are regardless if they fit the definition or not. Because that is one thing we all share is to be the person we are without judgement or criticism.

    Liked by 1 person

  3. Great! Great! All of our choices of clothes are ways of signalling things. But we are also sometimes signalling to ourselves as well as to the wider world. I sometimes wonder if it’s even possible to have a broad category like “crossdresser” that has any meaning.

    I still feel pretty much like a girl even when I’m wearing jeans and a t-shirt. I’ve never like the idea that there is some kind of uniform that I have to put on in order to pass some invisible standard of femininity. I just want to be myself!

    Liked by 1 person

  4. I have noticed that folks on the trans* spectrum are highly tribal.

    I’ve mentioned before that they remind me of metal fans, in a way. Like, there are metal fans that will insist that you aren’t a “true” fan of metal unless you like a particular minuscule subgenre of metal that was only practiced by three groups from Norway in the mid-80s.

    So much authenticity policing in the trans* community just isn’t healthy. And it is also the exact same kind of behavior that we’d all criticize if it came from the mouths of cis folk.

    Liked by 1 person

  5. Brilliant post and I agree whole-heartedly! We are all just people trying to find ourselves and just get by. And no, a kilt doesn’t do it for me. At least not without heels, bra, blouse, makeup, wig, etc, etc.

    Liked by 1 person

  6. Reading between the lines simply.


  7. I thought your appraisal of crossdressing thorough and interesting. I like you summation also, indicating (at least to me), that it is really a matter of differences, with no limiting number, and shouldn’t even be anyone’s concern other than those intimately involved. I try to tell my wife that it is only a matter of clothing to me, not sex, not trying to become a woman, or anything else. I love wearing feminine woman’s clothes, that’s what drives me anyway. Thanks for your blog.

    Liked by 1 person

  8. Hopefully, a little less as each day goes by ! 🙂

    Liked by 1 person

  9. Maybe you should check out
    (for men who want the freedom to wear skirts, dresses, kaftans, etc. as men)


  10. Good Afternoon Daniella,
    Your blog certainly covers a lot of material. After I read this post, I added to my blog a piece I wrote in 2012, with some updated remarks. It is about “Androgyny.” I hope you will read it. I sense you will “get” it. I once had some boots that your daughter might have recognized as well!

    As my understanding of my own attachment to CD becomes more enlightened, I realize that I am really more motivated to look like a woman rather than pass as one. I am proud of the work I have done to understand womanly attire, shape, and poise. I have grown confident in my sense of feminine style – all things feminine, so to speak. It is as though, feminine apparel, carriage, and presentation is genuinely what I am all about. Just like our appreciation for the arts, the cars we drive, the homes we inhabit or the gender-appropriate clothing we select, I feel as though my comfort with femininity is an inescapable component of who I am as a person.

    Thanks for your insight,
    Falecia A. McGuire

    Liked by 1 person

  11. I accept men who cross dress (as in, it’s none of my business who wears what), but I also struggle with it (as in, on some very basic level I don’t get it). Traditional 1950s-style women’s clothes were, for me, so imprisoning that I have trouble getting it through my head that anyone who wasn’t raised in the damn things might choose them. The broader range of what was acceptable for women from the sixties onward has been a real gift. As you just said eloquently, the clothes I described don’t come close to covering the full range of cross dressing, but in my responses I still find myself coming back to them.

    And having said all that, I don’t expect either you nor the world at large to wrestle with it unless you actually want to. I just thought I’d toss it into the discussion, for whatever it’s worth.

    Liked by 1 person

    • Fwiw I am no fan of the whole 1950s thing. Funnily enough the 1950s clothes sometimes/often go hand in hand with a desire to emulate the 1950s relationship dynamics. My (uninformed) contention is that those that wish to do so lack a real/meaningful insight into what that means. The idea of having decisions made for you is way more appealing than the reality and for me there is very little appeal.

      Liked by 1 person

  12. Outstanding! I am not sure anyone can isolate what crossdressing is now that women wear pants (since WW2?) and with all that we can see in other countries.

    Liked by 1 person

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