Crossdressing as a crossdresser… or as a woman?


What’s in a name? that which we call a rose
By any other name would smell as sweet;

— William Shakespeare, ‘Romeo and Juliet’

Ah, the eternal issues with the word ‘crossdresser’! How much significance we attach to a single word, and how often it describes us so poorly!

You all know that feeling: you’re in front of the mirror, applying the final touches of your makeup, perhaps putting the wig on, or finishing up the polish on your nails; no matter what the ‘last step’ is, at some point your mind goes ‘click!’ and you think to yourself: ‘There it is — a beautiful woman looking at me in the mirror’.

And maybe you might tweet or post on Facebook, ‘I’m going out crossdressed’.

Among fellow crossdressers, you might have a lot of expressions to describe your different modes of dressing: you might be ‘in male mode’ and en femme, or ‘in drag’, or simply ‘crossdressed’. In my own country there are a lot of different descriptions for a male wearing female attire, all slightly pejorative, but which the community has claimed as their own, and they have become so popular that it’s hard to get rid of them.

It’s not uncommon for communities to develop their own jargon; the Anglo-Saxon world is an excellent example of how the English language is constantly changing how we use words to describe new technology, new forms of leisure, new ways of connecting to others. I wonder if in twenty years we will still know the meaning of ‘googling’, ‘tweeting’, or ‘texting’.

The crossdressing community is obviously not different in that regard. It’s true that a lot of the jargon will naturally come from makeup, attire, accessories — things that regular cisgendered males are ‘not supposed to know’ since they come from the ‘secret sorority of Women’. But crossdressers (no matter the reason why they crossdress) have obviously a lot of ‘new’ words describing their activities. After all, cisgendered women hardly have any reason for ‘tucking’. And they don’t go out en femme — they simply ‘dress up’ to go out.

Now, I don’t really want to get into the much more deeply philosophical question of ‘what it means to be a woman’ (or a man, if you wish to ask that as well). Here I’m just going to stay at the surface: when we interact with others, we have a form of presentation — that’s what we wear, but also how we communicate with others, what body language we employ. Because we cannot fully read people’s minds yet (but scientists are really working hard at that!), we require additional ‘hints’ to figure out what goes on in other people’s minds. And this, of course, means picking up subtle clues on body language, behaviour, tone of conversation, and so forth.

We don’t need to go far: every kid knows when their mom is furious at them. They can certainly pick up emotions, and ‘read the mother’s mind’, if you wish. That’s because we’re good at evaluating facial expressions and body expression, as well as the tone of voice employed. But we don’t even need to restrict ourselves to the human species: our furry friends have no grasp of human language, but they certainly know very well when we’re angry at them (because they spilled the milk on the carpet again) or when we’re happy to play with them, or when we simply wish to be left alone. We, in turn, are actually also quite good at sensing their moods and feelings by ‘reading’ their body language — and the more familiar we are with certain pets, the better we can ‘read their minds’ (I’m pretty good at figuring out when our younger cat is thinking about doing another round of mishap — and he is very good at figuring out that I know what he’s thinking!).

Crossdressing, in a sense, involves a certain level of deception: by emulating different body language, communication forms, and attire, we ‘pretend’ to be something we’re not. Or, at least, that’s how most people view crossdressing — and that is the biggest reason why they feel so uncomfortable about it.

Well, but is this really what is going on?

The truth is that the ‘crossdressing community’ behaves as if they are, well, ‘crossdressing’, which somehow implies they’re being somehow deceptive by picking up the ‘wrong clothes’ for their gender. The Japanese have an interesting way of looking at things: if you crossdress as a fetish (i.e. for sexual reasons), then it’s something not really welcome. But if you crossdress as a hobby, well, then it’s just like cosplay — that’s perfectly legitimate and allowed. Everybody is allowed to cosplay as much as they want, and Japanese are, by now, quite comfortable with cosplaying.

In my own country, and probably that’s true for most of the Western world (especially where cosplaying is not so popular yet), it’s very hard for people to understand that there might be some other reason for crossdressing beyond a sexual fetish. A heteronormative cisgender male would ask: why would those guys go all the pain to put on makeup, wear corsets and clothes that are unlikely uncomfortable, and kill their feet on impossibly high heels — if not for sex?

The issue is that it’s perfectly normal to assume that people go ‘all the way’ doing insane things if it’s for sex, power, or money. Well, it’s how our society has been designed. We can’t change the way people think — they have been conditioned for way too long to be able to think out of the box.

Instead, we should actually explore that strange relationship between a crossdresser and their clothes.

Let’s look at the other side of the coin. Women ‘dress up’ (and men, to a degree, also do that, even though not to the same level of accomplishment). This somehow implies that women, in general, have at least two different modes of presenting themselves to society: in ‘plain mode’ (whatever that means) and ‘dressed up mode’ (again, whatever that means). In practice, women dress differently according to occasion, obviously; and they don’t wear cocktail dresses to gala dinners (or at least they shouldn’t), and most definitely dress differently when they’re going to impress a potential new boyfriend, or when having lunch with a husband they’ve lived with for two decades.

In all those forms of dressing, women still continue to be women. They’re not ‘less feminine’ because they aren’t ‘dressing up’, and this is a point where feminists insist: it’s only in sexist societies that women are ‘expected’ to be ‘dressed up’ all the time. Enlightened societies do not ‘expect’ anything from women: they dress up when they enjoy it, and they don’t dress up if they don’t feel like it. Some women dress up every day, because they love it; for most, they will only dress up for special occasions; and a large group (even though the smaller one!) will simply abhor ‘dressing up’ and will try to avoid doing so for most of their livetimes — excepting perhaps when attending the odd marriage or so (and they’ll complain about it for weeks).

Although there is definitely some social conditioning on what women are expected to wear (and this naturally changes according to the place, the time… and the fashion), there is not some kind of ‘universal feminising outfit’, i.e. a set of rules of dressing that will tell ‘this is a woman’. Sometimes, however, we tend to behave as if this is the case.

Expression is not identity… but they are correlated

To explain that a bit more, let me give you a personal example. Some years ago, in the middle of a conversation, I sort of told him that I was practicing Buddhism. He asked me if I was going to shave my hair and wear saffron clothes, at which I laughed, saying that only monks do that. Then he asked me if I was going to become a vegetarian and stop smoking and drinking alcohol. To which I obviously replied, ‘Uh, no, why should I?’

His answer, as you’re all going to expect, was the usual: ‘but I thought that all Buddhists had to be vegetarians and forfeit drugs (even legal ones)!’. This, of course, pushed me into a long-winded discussion about why ‘the cowl doesn’t make the monk’, or, to put it bluntly, exhibiting the exterior signs hardly imply that the interior is aligned to those signs.

But there is naturally a correlation between both. There would be little point for a Catholic monk to use the saffron robes of a Buddhist monk — the robes and the colours have special meanings for each kind of monk, and those meanings do not ‘cross over’ aming religions. Similarly, unless you are not familiar about why Buddhist monks wear yellow/saffron/red robes (and some don’t!), there is little point in ’emulating’ those monks by wearing the same garments they wear, and proclaiming to be a ‘Buddhist’ somehow because one’s wearing ‘Buddhist clothing’. The same, obviously, goes for all other religions, ideologies, and so forth. I get people wearing cool T-shirts with the iconic Che Guevara picture, and proclaiming themselves to be ‘lefties’, which I then confront with some maxims of their alleged ideology, and they quickly say, ‘oh no, no, I don’t agree with that’.

Another two stories about the same issue. I have a right-wing libertarian friend who in his late 20s loved to look like a hard rock singer/player — for a good reason too, since his younger brother was a hard rock player, and both brothers were reasonably good at playing. He liked to ‘break all rules’, wearing leather jackets and very long hair everywhere, even later at his job, and he definitely looked as a ‘rebel’, an outsider, a borderliner (with a personality to match). One day he was sort of walking with me and my eldest (female) cousin, and, at some stage, he mentioned that he was married (that happened a year or two before we met). My cousin wondered about that: she asked him if his marriage had been kind of ‘radical’? My friend admitted that it was a conventional marriage, going to the church first, then dressing up in pseudo-18th century fashion, and having a party at a very, very fancy place. The only ‘radical’ aspect of the whole marriage cerimony was that he and his brother played some hard rock for the guests. My cousin laughed at his ‘radicalism’ — so, after all, he had a conventional marriage, a conventional wife, lived in a conventional apartment, and wanted to have a conventional life? His ‘radicalism’ was just skin deep — his signature black leather jacket and his long hair. But, in truth, he lived just like billions of other people, and that kind of ‘normality’ was what he craved…

I guess this was one of the very few moments that I saw my friend unable to answer. He still tried to argue that one could be a ‘radical borderliner’ and still live a conventional life — but my cousin, who’s pretty smart, was not easily fooled by that argument!

Another friend of mine, years later, claimed to be a left-wing libertarian. I met him at our Buddhist community. Besides doing practice together and studying ancient Buddhist texts, we naturally engaged in all sorts of conversations. Politics was a popular topic; the teacher’s own father had been a very fundamentalist communist, and of course this modeled the teacher’s own way of thinking — until, of course, after studying the Buddhadharma (the teachings of the Buddha), he naturally dropped most of the ideological ideas, since they made no sense. Communists (even former communists) and left-wing libertarians tend not to go well together (but we had all sorts of ideologies in the group, and the teacher was good at discussing with all of them — a prime requisite for a Buddhist teacher!).

So this friend of mine also considered himself a borderliner. He was tall and skinny, and, because he picked up Buddhism, he shaved his hair like a Buddhist monk. At the time we met, he had gone through a divorce, had too teenage kids, had some issues dealing with drugs, but was putting his life back in order, and got a new wife (who also was part of the Buddhist group). He drove a bike and it was not uncommon to see him undress his black leather outfit to reveal red or saffron-coloured garments beneath; he was a strong supporter of the movements to free Tibet; and from time to time, he was a fanatical vegetarian.

During one discussion, he was exposing the fundaments of his ideological beliefs, in a casual way — how he was against unnecessary government, and against excessive regulation, and all sorts of limitations that governments tend to impose upon common citizens. As a libertarian — not an anarchist! — he saw the role of government as being useful in very limited cases only, but preferred self-organising communities: he was the kind of guy that was always coming up with ideas for the group to do on behalf of the community (many were actually put in practice, like fund-raising for buying food for poor people). In the middle of the discussion, however, someone mentioned his bike outfit. One should point out that his bike was very expensive, and so was his outfit; one tiny little fact that did not really go well with his claims of being a left-wing libertarian, who usually do not care about money (or spending money in ‘useless’ gadgets and toys). He sort of described its purpose: to ensure that if he had an accident, at least some of the more obvious things — skin bruising, etc. — would not occur. He certainly was all in favour of safe riding, and complained that a lot of accidents happened because people were reckless, putting themselves and others in danger. At that point, they asked him if his teenager daughters already had a bike, to which he replied, ‘of course not! It’s too dangerous for them!’

The discussion heated up. People in the group were saying that teenagers are, by definition, reckless; wouldn’t it be better for him to teach his daughters how to properly ride a bike? Because it would be just a matter of time until one of his daughters’ boyfriends took her on a ride, and how could he be sure that she would ride safely? He said that he forbade his daughters to do that; to which someone argued that he couldn’t control all the moments that they spent with their boyfriends; to which he responded that he didn’t allow them any boyfriends that he hadn’t approved; to which someone asked how he knew if they had boyfriends or not, and so forth.

And at some stage, when it was clear that he could not really ‘control’ every moment of his daughters, and grudgingly had to agree that it was possible that they would ride a bike without a permission, he came up with the following argument: ‘The Government should enforce that teenager kids ride bikes properly, so that parents can have their minds at ease.’

At this our Buddhist teacher burst out laughing. This baffled my friend, until the teacher said: ‘I thought you were a libertarian! But now you are saying that you wish the government to enforce rules! And rather strict rules as well, so that kids are always safe! That’s not libertarianism; that’s right-wing patriarchy!’

My friend didn’t ‘get it’ immediately. Surely, as a parent, he had the right to demand the protection of his kids? That, said the teacher, was not the issue. The point is that left-wing libertarians do not rely upon governments to do that. They protect kids themselves. Also, left-wing libertarians definitely don’t tell people how to live their lives, even if it’s for their own sake; such arguments — that the State is supposed to enforce how people live, behave, or even think — come from the right-wing. Not from the left!

Now this friend of mine was not half as clever as he himself thought he was, so he was a bit confused about the outburst of laughter, and the issue was dropped. Some days later, however, the teacher had the opportunity to discuss some of the points with me. Being a parent with a young adult as a kid, of course he could understand the issues of parenthood, the worries that people have if their kids are safe or not; he most definitely went through all those phases of anxiety, so he understood why our friend wanted ‘the government to protect kids’ (especially when the parents are not around them 24h/7, of course). But he lamented that so many people would somehow grasp at a certain ideology or philosophy, start wearing clothes or accessories (wearing their hair long or short, according to the ideology/philosophy), showing all sorts of outwards signs that they are deeply aligned with a certain point of view, but, in truth, they didn’t really follow those ideas or concepts. Their outwards behaviour was not aligned with their true, inner feelings and emotions. And it was not really hypocrisy. In most cases, it was a lack of understanding about what issues are relevant or not. As a Buddhist teacher, he was tired of seeing students ’emulating’ the teacher — growing beards or shaving the hair, dressing in the same kind of clothes, even going so far as to drink the same brand of soda, and so forth — instead of actually doing any practice…

Anyway… I’m almost losing my train of thought here. All these examples are only illustrating the same point: there is a correlation between identity and expression, but expression, by itself, does not imply identity. It’s just what we can see that gives us a clue on how people are.

And here is where we start diverging (again) on the meaning of the word ‘crossdresser’. By definition, it means ‘someone dressing as a person of the opposite gender’. Well, yes, but how accurate is that description?

The world of crossdressers

When I started crossdressing, it seemed that crossdressers had a world of their own: I quickly found out about websites offering ‘clothes for crossdressers, because men are shaped differently from women’. That sounded logical, so I naturally bought some of those overexpensive clothes, most of which out of fashion for about two decades, but I didn’t care: I was happy. I was crossdressing. That was what mattered.

I also got a lot of ‘makeup for crossdressers’, as well as all kinds of tools and accessories ‘made for crossdressers’, from breastforms — naturally! — to very weird undergarments that are supposed to shape-shift your positively male frame into something that looks much more female. Some of those are true instruments of torture. I also got wigs ‘specially made for crossdressers, since men have, on average, larger heads’. I even bought fake nails from special online shops for crossdressers (as well as nail polish), because, well, I thought that somehow they would be ‘different’ than the kind used by genetic women.

There was some truth in some items. For instance, I couldn’t pierce my earrings, so I needed ‘special’ earrings that had clips instead. But the ‘crossdressing world’ offered new designs, that looked ‘just like normal earrings’, with cleverly designed clip-like attachments, which didn’t look like clips at all, but emulated quite well what a clip-less earring should look like — without the need of punching a hole through my earlobes. That made sense: you couldn’t get them anywhere in a shop (at least, that was true of the mid-1990s in my country). And naturally, no shoe shop around here would carry the insane sizes I needed for my feet!

I believe that the only item I had back then which did not come from a ‘crossdresser shop’ was the cigarette holder and lighter — because, well, I guess that the number of crossdressing smoking fetishists is way too small for those online shops to bother with us. But even my handbag came from one of those shops as well.

It’s true that by then I was way too scared to search for clothes and accessories on real women’s shops (although I very early bought a jacket that way). And I had no idea about sizes — especially on how women’s sizes correlated to my male frame — so I needed some help from those crossdresser online shops which were obviously very CD-friendly and happy to explain everything in detail. And, for that, they charged premium.

Still, when looking at pictures of fellow crossdressers on the emerging Internet, it was clear that they all shopped from the same places. It was really easy to spot what had been bought on those shops — they didn’t carry that much choice back then, of course. But on the other hand, there was a sense of ‘belonging’. We were men who dressed as women, and we ‘had to’ shop at the same places — because there was ‘no alternative’ for us — so we somehow tended to look alike, with the same wigs, the same clothes, the same shoes. We were part of a special sorority, and our clothing tended to define us as members of that group.

After some years, I was fascinated about the vast amount of offerings that existed for crossdressers around the world — but most especially in the English-speaking world. There were beauty salons, specialised in doing extreme makeovers for crossdressers. There were whole neighbourhoods with brick-and-mortar shops just for crossdressers, in some of the more tolerant cities in the Western world. Crossdressers would go to crossdresser clubs, or even sometimes to crossdresser restaurants, to spend a quiet evening together. There were hotels and even cruises, all designed for crossdressers to come together and have a good time, and enjoy being crossdressed, hang out with friends, in a tolerant environment. I was truly fascinated, since that was completely outside my experience.

Crossdressers surely had some great time, in all those fascinating, enlightened, tolerant, but far-away countries! I was jealous of them, but also glad, in a sense, that at least in some parts of the world, crossdressers could have a great time together!

I was also eagerly reading the many studies that started appearing about crossdressing and transgenderism in the mid-1990s. A lot of it was plainly wrong, some of it was incomplete, but at least on the sociology/anthropology side of things — as opposed to the psychological one — there was good research being done. And it showed pretty much the image I already had: that crossdressers somehow lived in a world of their own, a world where they could dress the clothes they liked, and go out with friends, and be accepted for what they were.

The same also happened with clearly transgender individuals. Most seemed to live on the fringes of the crossdressing world, but they also had a ‘ghetto’ of their own: the society of similar-minded individuals who were beginning transition and would support each other, often around a formal association to help individuals in transition. One thing caught my attention while reading those studies: a lot of transexuals (remember, I’m talking of research done in the 1990s!) seemed to ‘stay’ in the ‘ghetto’. They applied for the real-life test by doing volunteer work ‘for the community’. Many cases were reported where the transexual would sleep inside the offices of a support organisation — possibly on a back room — and would work as a volunteer in order to qualify for the real-life test; then they would happily go through all the hormone therapy and surgery, and continue their lives saying close together to the organisation which supported them. They did that not only because of gratitude, but mostly because they feared the transphobia of the ‘outside world’

Some sociologists and anthropologists found this behaviour a bit odd. After all, these people did not really become ‘members of the opposite gender’ in the sense that of the gender role — a role which implies full participation in society in general. Rather, they ‘stepped out’ of society altogether, and created their own safe environment, where they could be themselves outside of society, because they feared that society would never accept them as they are (and in most cases I can understand those fears — they would be fully justified!).

This naturally created a problem for the psychologists. Would it be ethically acceptable to ‘allow’ transition for an individual, to relieve them from the adverse effects of gender dysphoria, but ‘condemn’ them to a life in a ghetto, sheltered from society-at-large? Some psychologists and psychiatrists were unsure about the long-term effects of that scenario — and they also feared that ‘cult-like’ effects could manifest themselves, with the negative consequences associated with those (co-dependence, for instance).

In fact, there were plenty of reports of cases like the following: an individual started crossdressing at home, when the urges to do so were overwhelming. He feels very guilty about it. But by chance he came across an ad for an organisation or support group. He timidly joins one of the support groups, not sure about what to expect. But he quickly figures out that this is the right place for him. The organisation has plenty of rooms where he can crossdress in safety. There might even be makeup tutorials, dresses and wigs to borrow, and someone willing to show how to walk in those 5″ stiletto heels. The organisation is also even willing to act as a pick-up address in case they wish to order something but don’t want it to be delivered at home. And, of course, there are makeover sessions, photo sessions, a monthly dinner, and so forth.

The individual is astonished and incredibly happy: this is all he wanted in his life, a place to be able to be what he always wanted to be — a beautiful, glamorous woman — and be surrounded by others, in privacy, who also have the same urges.

After a few months, this person is given some gentle hints that there is more than merely putting on women’s clothes and a wig. What about growing your own boobs? What seemed to be completely impossible just a few months ago might now become a reality. Members of the organisation start giving some hints that a few of them actually live like women full-time and have gone through transition; and they would be happy to do the same for all other members, if they wish.

In some cases, these are more than ‘subtle hints’. They may come to the point when it’s ‘expected’ for members, especially those that have been around for a few years, to go ‘the next step’ and become ‘trans women’. Some might be unsure about that step. Others might have come to a turning point in their lives: losing their jobs, going through a painful divorce. What is left? The friends at the organisation who always have supported his crossdressing. So now he needs to grow boobs and chop his genitals away? Why not? It’s not as if he has anything to go back to, anyway; he might as well become a woman and continue to support others, while at the same time ‘ascending’ in the hierarchy of the organisation…

Written like this, it seems like these organisations are something terrible! In reality, this is just how some sociologists perceived those organisations, many of which don’t even exist any longer. And those cases might have been extreme ones, glimpsed by the researchers in the field — they certainly are not representative of the vast majority of support groups out there!

However, there is definitely something which the researchers have stumbled upon, and which is not totally incorrect. There is a sense of ‘belonging’. I have to admit that I have only felt that very recently, since for most of my adult life I only crossdressed by myself or in front of my wife. It takes ‘being part of a group’ to understand group dynamics, to be able to study them and experience them, to form some bonds and let them grow.

My own group was at the verge of dissolution at some point, and I could see how strongly it affected most of the people (including myself). They had waited years for something like this, and it seemed a waste of time to let it go, just because some idiots were doing dumb things and playing their little games of power.

But the reverse was also true: new members came with a slightly different vision about crossdressing, and, very slowly, this vision tended to be adopted by all members. Even if they didn’t fully agree with it, they at least accepted with it in general. And, like all groups, all communities have rules. Such rules emerged spontaneously, but at some point they started to get written down, and members were supposed to follow them. This, by itself, does not mean much. However, we ought never to forget that ‘society’ is nothing more than rules, rules shaping roles.

From ‘man in drag’ to ‘expressing one’s inner female’

At some point in my life as a crossdresser (I can’t pinpoint exactly when), I remember that I wanted a new dress, but there was nothing on the usual sites with clothes for crossdressers that looked remotely like what I had in mind. So I bought one from a mail-order catalogue (later, this company would have their own website). My thoughts at the time went like this: so, sure, I don’t have a female frame. But there is no ‘standard’ woman’s body; women come in all sizes and formats! Surely there must be something that they can buy that fits them? In my case, this mail-order catalogue also had ‘clothes for the larger woman’, so I thought that something from there would fit me — perhaps not so well as the clothes from the crossdressing shops, but it would be better than nothing. Also, of course, it was cheaper — way, way cheaper, and I’m not even taking into account the shipping costs. For the price of a ‘crossdresser dress’ I could easily buy 3 or 4 ‘extra-large woman’s dress’ (these days, it’s more like 7-8 times…), and I had way, way more choices: surely something would fit me?

Not surprisingly, of course, it did fit, and not too badly, either. Frowning, I raised an eyebrow at all I had learned about crossdressing so far: was it really necessary to get all that stuff from sites specifically selling for crossdressers?

At that point, I realized that I didn’t really want to be a crossdresser, in the sense of what that word evoked in my mind — a ‘man in drag’. Not necessarily a ‘drag queen’, but someone who was clearly male and clearly wearing female clothes. Instead, what I wanted was to pass. That meant dressing as a woman, not as a crossdresser.

Now this required tripping a mental switch somewhere, and I’m aware that many, many crossdressers will never do that. They will remain all their lives happily ‘dressing as a crossdresser’, unaware that there is a difference. And the difference is actually stepping outside one’s comfort zone and embracing the wide world — as a woman, not as a ‘man in drag’.

Some of you, at this point, might claim that such a quest is impossible; some people will never look like a woman, no matter how hard they try, because they’ve simply got the wrong body type. Well, I don’t fully agree. Once the wide range of women’s clothing is embraced, there are always something that will fit. As said, women also come in all kinds of shapes as well. And women are very clever: if the shape doesn’t fit the dress, you can always change the shape, and yes, that means wearing shapewear — which has come back into style once again, since not all Hollywood starlets have those gorgeously trim and fit figures that people think they have. And if they are allowed to use shapewear, so do we. In any case, there are really many, many choices. The really tough issue is that we will be limited to the choices that fit — which means that those kinky little black dresses for impossibly small waists are probably out.

A crossdresser dressing up as a crossdresser is able to choose pretty much what they want to wear. After all, nobody cares if they look ridiculous or not. They’re fine in wearing prom dresses — or even wedding dresses! — to a private crossdressing event. 6″ heels on 2″ transparent platforms are widely available in large sizes — that means that crossdressers buy them in spades, and are more than willing to walk in them. It’s fine to dress like you’re 15 even if you’re 55. In the world of crossdressing, pretty much is allowed — and you can go the full range, from cosplay to drag queens, from gothic lolitas to prom queen. Everything is allowed; nobody will ever say anything — except to compliment you!

But when you’re dressing as a woman, the rules change. If the purpose now is to pass, that means understanding clothes (and makeup, and accessories) like women do. It means understanding what you are supposed to wear in public, considering your body type, your figure, your age, and the occasion. It does not mean having less choices: it means that among the infinite range of choices, some are adequate, some are not. It means rules.

For many crossdressers, these rules are meant to be broken (after all, genetic women also break rules): you’re supposed to be allowed to dress whatever you wish, after all. To stick with stupid rules, you have always have to endure your ‘male mode’. When en femme, well, all rules are automatically broken (by definition), and why should anyone have the right to create new rules just for crossdressers? After all, what’s the point in attempting to pass, anyway? Is that even a worthwhile goal to pursue?

There is, of course, no right answer to that (neither there is a wrong one). There is, however, a social answer. In my experience, crossdressers who are willing to respect society’s norms about what a woman is supposed to be wearing (depending on occasion, body type, and age) will earn respect in return. That means they will be far easier tolerated and less prone to discrimination — even if they are ‘read’. The issue here is that one can make an effort to behave as a woman in public, and that involves a lot of things besides wearing nice dresses, and this will lead to higher degrees of tolerance and acceptance. It does not mean ‘putting on an act’ — we can still be ourselves, obviously, and just express our inner female according to our own personality. What it means is doing what every other genetic woman in the world does: within a certain framework of rules, establishing one’s own style, being creative about our appearance, bending rules but not breaking them. This is what society expects of genetic women; and this is what we can strive to emulate.

The inevitable rift

It’s clear that the above thoughts will separate two different kinds of crossdressers: those that wish to ‘pass’ (no matter if they actually pass or not; the point is that they make an effort to do so), and those who have absolutely no intention to ‘pass’ but merely to enjoy whatever they fancy to ‘feel feminine’. The first group wants to step out of the ghetto: they wish to interact with the public-at-large, go to ‘normal’ places like any other female, and be accepted — or at least respected and tolerated. The second group has no such intentions: they merely wish to enjoy themselves in projecting their inner female, no matter if it ‘breaks all rules’ or not. They’re fine with private environments where everybody else has the same outlook in life; they don’t ever wish to go out in public (for various reasons), unless, of course, it’s Carnival (or Halloween) and there is no fear in looking ridiculous in public and attract a few laughs.

Both groups will naturally claim that they are ‘true crossdressers’ — in the sense that they do fully dress (as opposed to partial crossdressing or ‘underwear’ crossdressing), they act and behave in a different way than in their male mode, and they wish to socialize and have fun with similar-minded individuals. But the first group is not really ‘crossdressing’ — in the sense that they remain ‘male inside, female outside’. Rather, they dress as women, to reflect their inner image as women.

Some might say that there is a fine dividing line between both groups — after all, most will start on the second group, some ‘evolving’ towards the first, others remaining happy as they are — and that there is another fine dividing line between the first group and a transgender individual. I agree, there is much more ‘blurring’ than ‘lines’. Ultimately, each crossdresser will answer the following question to themselves, trying to be as honest as possible:

When I dress up, do I dress up to look like a woman or to look like a crossdresser?

It’s not a very easy question to answer. From my experience, a lot of crossdressers believe they are ‘dressing like a woman’ but they are actually just copying the styles they see from fellow crossdressers. I know: I’ve been one of them!

There is an acid test that one can do with those who ‘crossdress’ as opposed to ‘dress like a woman’: ask them to compare the way they dress and behave to the genetic women they see on a daily basis. Do they dress and behave in the same way? Someone who merely ‘crossdresses’ will simply say that ‘genetic women are different’ or that ‘they have an individual style’ or something like that. Or they will flatly enter in denial, claiming that ‘they look awesome just like that’ and caring little about how genetic women look like or how they behave. By contrast, someone who ‘dresses like a woman’ will humbly admit that they are trying very hard to look like genetic women, emulate their dress style and behaviour, but still not there yet.

I certainly have come across both types quite often. There is a huge difference between ‘being a beginner’ — and admittedly doing a lot of things wrong, just because one has no experience — and deliberately not caring about how real women look and behave. Sometimes it’s not easy to distinguish between both. Often someone might claim that if they just had the right makeup and the right dress, they would look exactly like genetic women (when it’s clear that they would not). What should we think about those claims?

A certain degree of humility and, most importantly, the will to learn — keeping an open mind, no matter for how long one has been crossdressing, knowing that there are always new things to learn — usually are tell-tale signs of those who wish to pass as genetic women, as opposed to those who simply want to crossdress. But that’s not always the case: some who just wish to crossdress will probably have an inner image of what they would like to see in the mirror, and might strive to accomplish that — no matter if that inner image actually reflects a real woman or merely a fantasy of what a woman is supposed to be.

Such distinctions, of course, do not entail any moral valuation. It’s not ‘right’ or ‘wrong’ to be either of those two types of crossdresser. Neither is ‘better’ than the other. It’s even hard for me to say how many would fit on one type, and how many on the second type. It’s clear that fetishists, for instance, usually have no intention of really, really looking like a ‘real genetic woman’ — but there are huge exceptions: in some scenarios, fetishists looking for sexual partners (usually heterosexual males) want to express themselves in a way that they are utterly indistinguishable from genetic women — and often they really succeed, as we can see on many pictures posted on the Internet and on many YouTube videos.

The main issue is probably one of ‘getting accepted’. Respect and tolerance come mostly from behaving according to ‘expected behaviour’. Crossdressers trying hard to look and behave like real women — no matter what their body figure actually looks like, or how ‘good’ they are with makeup and fashion — will very likely be more tolerated by a narrow-minded public, because they will at least see some familiar things in their attire, body language, and behaviour, and might say things like — ‘I disagree with men dressing as women, but at least some do it elegantly and are not disturbing the peace’ (women, in that regard, are far more tolerant than men). By contrast, those who dress to shock and provoke reactions from passers-by in public, will very likely risk a higher degree of intolerance. Those who simply wish to be left in peace and enjoy their female self-image — no matter how accurate that image might be, compared to ‘real genetic women’ — will most likely do it in private, away from the public eye.

The fear of getting mislabeled… as sex workers!

Borderliners don’t help, either. In my country, crossdressing prostitutes are becoming increasingly popular. A bit more than a decade ago, transexual prostitutes started to become available on selected environments; they would also be seen sometimes in certain quarters of the city, which started to become famous for ‘unusual’ sexual partners. But transexuals are few in number. By contrast, there are far more crossdressers, and it should not be surprising that those would get customers far more easier (and vice-versa, it is far more likely for a prospective customer to get access to a crossdresser than to a transexual person). What happened is that crossdressing prostitutes lost their fear, and prowl not only the streets in certain quarters, but they even go to popular shopping malls. Some of them, of course, are very easily spotted; some less so (customers will of course know where to find them and who they are, in this era where the Internet is so useful to set up dates…).

It’s not as if crossdressing prostitution is widespread, I just mention it because it is popular enough to have become more and more visible in the past few years (maybe because the financial and economic crisis pushed a lot more people into prostitution…), and it means that what the public sees and knows are crossdressing prostitutes. They might even understand that there is a difference between them and female impersonators on stage. But it’s impossible for the public at large to understand the difference between a crossdresser who just wants to go out with friends, have some dinner, go shopping, have a drink, and do pretty much exactly what half the human population does when wanting to have a good time; and those crossdressing prostitutes, who show themselves in public, waiting in front of some shop or inside some bar for potential customers. The two kinds are not easily distinguished.

Of course there are a few visual differences, namely in the dressing style, and probably also in much of their body language as well. They are, after all, looking for customers.

This means for our group that extra caution is required. While obviously we cannot interfere in the freedom of expression that everybody has in our country, and while naturally anyone is allowed to create their own female self-image as they wish, there is no other choice but to set some rules in place. And a simple rule is that while everybody is allowed to dress like they wish in private, when in public, and within the context of our group, and the places we go, it means dressing like a woman, not like a whore — or some weird cosplay/bizarre/grotesque image of a woman. For some, telling them such ‘rules’ may be very offensive. In that case, we do it like the Beaumont Society does for their members: you either obey the rules and are welcome to go out with us, or you stay at home, or go out with different groups who have less strict rules.

This is tough for many, who expected more ‘tolerance’ and ‘open-mindedness’ from fellow crossdressers. But it’s not about saying who is right, who is wrong, who is open-minded, who wishes to ‘control’ operations. This is much more about dealing with pragmatic rules. We crossdressers are already bending too many rules, and we still wish to get accepted by society. That means we also need to accept society’s rules, and make them our own. At least, as far as we can.

Rules to survive in a rule-dominated society

I forgot what science fiction author once wrote: ‘In hard science fiction, you have to strictly follow all laws of physics — you can break only one for the purpose of the plot’ (soft science fiction, or technofantasy [like Star Wars, for instance] are free to break as many rules as they wish). The purpose is mostly to make the plot and the message convincing — the ‘what if’ scenario is supposed to only ask one question (i.e. What if we could go faster than light? What if we could develop anti-gravity?) and focus the narrative on that physical law that was broken. If someone wants to break 3 or 4 laws at the same time, they should simply write 3 or 4 different books instead. There is a concept in literature known as suspension of disbelief: the author tries to convince the audience that they are relating a believable story, and not merely fiction. The more rules are broken, the more the narrative deviates from reality, and at some point, the suspension of disbelief falls apart — the story stops to be believable anymore, and the reader gets bored.

There are a lot of excellent movies that are very, very good at using suspension of disbelief to make them very credible, and, therefore, engaging. Knowing how to ‘bend’ reality so that the audience still ‘believes’ the narrative requires a lot of ingenuity. It’s not easy to do. Thus the rule of those old hard science fiction authors: just break one rule. It’ll be easier to make the whole narrative more convincing.

Crossdressers also create their own narrative. But to make it simpler to be accepted in society, we ought just to break one rule: the rule that ‘forbids’ men to dress like women. That’s the single rule we are breaking. But we can — and, if we wish to be accepted, we should — keep all the rest of the rules. That means learning what rules pertain to the female gender role, and accept them all, and incorporate them in our own narrative.

Obviously most women also ‘break rules’. In art, it’s supposed that you learn the canon — the set of rules of your particular artistic field. Things like how to do perspective, for instance. Or, in music, how to do polyphonic harmony. Then, once you have mastered the techniques inside the canon — not merely became familiar with it! — you’re allowed to break the rules. Geniuses are supposed to be able to advance art by breaking formerly established rules. However, first you must be a recognised genius in your field; then you can start breaking rules.

Therefore, I would suggest that first crossdressers ought to present themselves publicly by showing willingness to comply with the so-called ‘rules of womanhood’, according to the society they live in. That should be the first step, even if they disdain internally all rules, are against gender, and demand that society accepts them ‘as they are’. That should only be the second step, not the first. It’s easier to accept a Caitlyn Jenner and only afterwards accept a Conchita Wurst (yes, I know I’m mixing apples and oranges — Caitlyn is a transgender person, Conchita is a stage performer and singer).

At least it’s easier if one starts by following conventions in public, while reserving the rule-breaking for a more private environment. Imagine how people would react if they saw BDSMers whipping their slaves in public and dragging them around in shopping malls with a leash and collar — at least, outside Carnival or Halloween. Sure, a few do exactly that, and ‘demand’ respect and acceptance. But most BDSMers present themselves socially as any other person. Perhaps one of the reasons that BDSM is so much accepted is because of its private nature — it happens all outside the public eyes. The more serious the BDSM practitioner, the less likely he or she will have a Facebook account with their profile picture snapped inside their private dungeon at home. It’s mostly those who are new to the community that brag about their ‘rights to be different’.

The same should be the goal of every crossdresser, ‘beginner’ or ‘veteran’. When presenting in society, they ought to present themselves ‘as a woman’ — and not ‘as a crossdresser’ — no matter if they ‘pass’ or not (which is not really germane to the issue). In any case, they ought to learn what it means to adopt the female role and present as a female in public; fortunately, there are plenty of tutorials for that, and, of course, having good powers of observation — or a few helpful friends, genetic women and crossdressers alike — will definitely help quite a lot along the way. Naturally, when in private, in a closed group of fellow crossdressers, then of course they should be free to express themselves as they wish, and forget all about society’s rules.

The difficulty here is that each person applying the label ‘crossdresser’ to themselves will have to understand quite clearly that it means completely different things (and sometimes even opposite!) to different people. But there is usually a common set of principles to which everybody can adhere and make their own. In general, MtF crossdressers will (at least partially) want to express themselves as women in some way. A secondary goal is to earn at least some respect and tolerance — or, at the very, very least, some indifference (i.e. being left alone and not being bothered by transphobes). If that gender expression occurs in public, it will mean sticking with the rules that society set for the female gender, at least to a degree where both the attire and the attitude are minimally recognizable as being female. That requires some training and some learning; any crossdresser wishing to present themselves in public ought to make at least a minimal effort to do so.

One might ask ‘why’ this is necessary. After all, we live in Western societies where freedom of expression usually includes attire and behaviour in public. The problem is that legislation is often at an ethical level far above of those who live under a democracy; I’ll refer to Kohlberg’s stages of moral development to understand why that happens. So, while in a democracy everyone has the de jure right to present themselves in public as they wish, de facto most of the people will expect certain stereotyped behaviour according to the many roles inside society, and if you stick to those roles, you’ll be much better accepted. Men still wear business suits for their job interviews, even if employers are supposed to look at what your skills are, not what choice of clothes you wear. Conforming with social norms is important because they will generate expectations towards you.

Arrrgh! But I thought that being transgender meant getting rid of the heteronormative cisgender society!

Not everybody crossdresses for social activism. This also reminds me of another episode in one of my Buddhist classes, when one newbie came with a T-shirt saying ‘Free Tibet!’. He definitely saw the teacher frowning, and wondered why. The teacher then explained that more important to free Tibet was to free oneself first; but as this required a lot of explanations, he prefered to lecture on how social activists might not necessarily be good Buddhist practitioners, or how good Buddhist practitioners might not necessarily be good social activists as well — both things are completely not related. I still get a lot of conversations like: ‘Oh, you’re a Buddhist? Wow, that’s great, I’m all for freeing Tibet, too.’ Depending on the person, I’ll have to patiently explain that I’m not a Buddhist because I want to free Tibet, but because I want to free everybody from their mental delusions 🙂 This usually baffles them…

In any group with transgender people — even if they don’t label themselves like that — there will always be a few activists. Some of them will very strongly defend their right to overthrow the heteronormative cisgender society. Some might even be doing that actively — joining activist groups, doing marches, subscribing petitions, doing demonstrations in front of parliament, and so forth. Others might not be so politically engaged, but still have very strong convictions regarding the future breakup of this society which oppresses transgender people, and, as a consequence, they are very vocal about questioning gender and gender roles, and refusing to accept compliance with those.

Although such people are very vocal — like everybody with a cause, they engage in all sorts of activities with all their energy put into their cause — they actually don’t represent the majority of transgender people, even if they claim to do so. The simple truth is that most transgender people do not want to live in a genderless society. They’re fine with binary gender. They are just not happy to be stuck with the gender they were assigned at birth. There is a huge difference between wishing a different gender expression, role, or even physical attributes, and wishing to live in a genderless society. There is a huge difference in wishing for more tolerance towards those who are unhappy with being stuck with a certain gender, while still being fine with bi-gendered society, and wishing for tolerance towards those who reject a bi-gender society altogether. In other words: while eventually the ultimate goal is to have a genderless society, that’s not what we have right now: at this stage, we should be happy if people accept us or at least are indifferent to our existence — as opposed to being actively transphobic towards us.

So, leave the activism to the activists. As a crossdresser, it’s more likely that you’re fine that women are women and men are men, it’s just some of us are either not born in the right gender, or are not happy with staying in the same gender forever. We’re fine with shaving both our legs and beard if we wish to wear a dress and go out in public. We’re fine to be addressed as ‘ma’am’ if we present as female, and ‘sir’ if we present as male; we don’t need complex pronouns like ‘zis’ or ‘xer’, and don’t expect everybody to use those forms of expression when referring to us.

But if we expect to be addressed as ‘ma’am’ when wearing a dress, then it means dressing and behaving like a ‘ma’am’ in public.

If we just dress as women, but behave as men, then we’re just ‘males in drag’ (which is fine!).

If we want to get accepted as women — even if only as a ‘special kind’ of women — then it means doing a little more effort than that!

It’s a bit unfair for me to criticise others, but I’ve seen a lot of transgender people (and met a few of them) who get incredibly upset when they’re misgendered in public. Some of them post pictures of themselves, and I can only say that I would misgender them as well — because they give no exterior clues (neither on their attire, nor on their body language) that they wish to get addressed as the gender they identify with. Because we are not so good at reading minds (as said before!), we can only address someone based on their gender if their behaviour, attitude, and attire is conforming with that gender. In some cases, I have personally met a few of those persons — often claiming to be ‘very feminine’, and bragging about it all the time — who actually dress rather well, and are pretty good with their makeup techniques, but talk and behave like the rowdiest of males in public, and their body language is all wrong for someone claiming to be ‘very feminine’. Of course it’s to be expected that they are addressed as males — even if they actually wear dresses that fit and are appropriate for their gender.

It’s not that it requires overdoing. Look at Caitlyn’s videos. Her voice is not feminine; her gestures are not overly stereotypical feminine, either (and, these days, such exaggerated gestures are out of fashion, except perhaps among certain social classes or some groups). But her body language is consistent with her figure and her dress style; nobody would hesitate to call her ‘ma’am’ in public, even if she weren’t famous. She doesn’t need to get all the little tiny details right (especially not now, when she hasn’t had that much practice of going out in public as a woman). But she shows that she’s making an effort. And it’s undeniable that one can be an activist of transgender rights and conform to the rules and roles of a heteronormative cisgender society!

In short: if you are absolutely convinced that your goal in life is to subscribe to gender activism, then, by all means, dress and behave as you wish, but be aware of the consequences — don’t expect that you’ll never be misgendered if you’re actively fighting the heteronormative cisgender society and refuse to abide by their rules.

If your goal in life is to present yourself as a woman — embracing your gender expression as female — then it means sticking to as many rules as you can in order to express yourself as a person of the female gender role. That requires a bit more effort. But the result is that you will get more tolerance and acceptance that way.

If you just wish to have the opportunity to wear women’s clothes, but don’t care or don’t even want to be accepted as a woman, then forget everything I’ve said so far — it doesn’t apply to you 🙂

Just remember that not every crossdresser thinks like you do.