I’ve always envied the way one my best friends can easily strike up a conversation with another woman she’s just met. Obviously, this isn’t dependent on gender. My friend is gregarious while I’ve always been social awkward around strangers. (Yes, despite being raised in California, I’m one of Garrison Keillor’s people.) But it does seem like there’s a big difference to the way two newly-introduced women interact compared to two guys.

The reverse is also true. I know many genetic women who envy men’s freedom to move in safety—something I didn’t truly understand until going out en femme.

Maybe this is one reason it’s difficult for women to understand why we do it. Partly, I think we’re not always able to clearly articulate some of these things precisely because they’re so “ordinary.” Partly, it’s when we do, women have a hard time seeing why these sorts of things might be special to us—I’ve often heard genetic women express puzzlement about our attraction to make-up. Of course, there’s also a big difference wanting to do something—like wearing skirts or make-up—and feeling obligated to do it.

Of course, like any other “grass is greener” feeling, it’s envying something that sometimes is illusionary, in part or in whole. My friend can be far cattier about other women—including those she just chatted merrily away with—than I would ever be. Likewise as any guy knows, thugs and bullies will happily beat up on a “weak” guy. And if they really want to prove they’re tough, they’ll start a fight with the biggest, baddest dude around. Transman Raven Kaldera relates how a fellow transman learned this the hard way. As a butch lesbian, she could get in guys’ faces and they’d back off because she was a woman. As a man she got decked immediately.

BTW, I intentionally used the word “envy,” which is a complex emotion. It’s both a grudging admiration and a painful desire for another’s advantages mixed with a simultaneous discontent and resentment at their advantages. In relationships it often involves love/hate. Love for your partner and hate for the power they have over you.

Years ago Nancy Friday wrote in her book “Jealousy” (which really focuses on envy and power relationships): “Today, many women don’t need men, either for their money or for their sperm, given society’s tolerance of women having children on their own. Men’s envy of our new found power may lessen as they get into women’s traditional areas of strength, namely beauty and the rearing of the children, but it hasn’t happened yet….We don’t yet have that new social structure. Returning to Patriarchy is out of the question, but as a new power structure emerges to replace it, we must understand more than ever the furies our dismantling of Patriarchy have released. Our fury at powerlessness—our envy—is stronger than ever, stronger than any feelings of love. The truth is that we cannot love until we understand envy and its relationship to jealousy.”

In that light, we crossdressers are at least open about our envies while in other men it often festers beneath the surface unacknowledged, even to themselves. We take those things we envy and make them our own—at least sort of our own, since we’re doing them en femme rather than en homme.

Sometimes it’s not pretty. As Kaldera says:

Sometimes when you drag out an opposite-sex persona – so to speak – you find that it’s been stashed in the same mental closet as all the things that you don’t like about the opposite gender, and they’ve become stuck all over it like barnacles, or growths. They won’t flake off until that persona has been exposed to the air for a while, and gotten a chance to rub up against real people and real circumstances. This may mean plowing through years of humiliating stereotypical behavior until that part of you evolves and grows into a fuller human being. I’ve seen it again and again, especially in people who are just starting to cross-dress or whose CD persona only gets out once in a while. Stereotypes abound: the trashy whore, the catty and manipulative upper-class bitch, the irresponsible little girl, the supported housewife who never has to work or deal with the outside world, the delicately passive – and utterly useless – ornament, and, of course, Mom. In the bedroom, the sexual stereotypes can be even more cartoon-like, from Sweet Gwen the Victim to the Dragon Lady, but is most commonly the passive, receptive do-me-queen that men don’t usually get to be. Sometimes their personas are clearly signposts pointing to the issues that they are bravely working through.

Women are often horrified and offended when men deliberately imitate women, whether it’s a female impersonator in a drag performance or a fetishistic cross-dresser in ratty nylons and a bad wig. They feel that these performances of female gender are a bad caricature, and don’t actually resemble the real experience of women. While it’s true that a performance, or even a persona, is by definition shallower than a person, there’s still a grain (or a sackful) of truth to these performances. For every one of these stereotypes being performed by men, I’ve met the same ones being performed by women, and in larger numbers. I’ve met the biologically female version of every one of these caricatures, and I’m sure that the women who complain about the guys in dresses probably have, too.

The one silver lining of envy is that by pointing out where we feel inadequate we can choose to address those perceived inadequacies. Instead of coveting the characteristics we wish we had, we can develop them for ourselves. Likewise, we can move from begrudged admiration to respectful appreciation when we see those qualities in others.

So what things taken for granted by the opposite sex do you envy?

To briefly summarize, Hollander convincingly makes the counter-intuitive argument that since the late Middle Ages men’s clothing has been the fashion innovator—and that women’s styles have been both imitating it and borrowing from it for centuries. Before the 1200s, both sexes wore roughly the equivalent clothing: bag-like garments that were variously wrapped, belted and fastened. The length might differ—men often wore shorter ones for activities, such as physical labor and war, that required greater movement—and Northern European men added loose-fitting leg covers to cope with the climate, but the similarities far greater than the differences.

It was the under-garments invented to protect wearers of plate armor from their metal casings that sparked a revolution of closely-fitted garments for men that culminated in the “modern” men’s suit, invented around 1800. The wildly varying experiments in men’s clothing—compare the portraits of Henry VII, Rembrandt and George Washington—also reflected a “modern” sense of Fashion (with the capital “F” as Hollander refers to it through the book), which has an insatiable desire to move on to something new and different than what people are wearing at the moment. Whereas women’s fashion, while inventive in surface decoration and accessories, and incorporating the concept of Fashion, remained unchanged in the fundamentals until the 20th century—when women finally appropriated men’s fashion wholesale for their own use—although even today women’s fashion retains an emphasis on “using ornament and color according to expressive inclination” that was once the common to both genders.

But people generally don’t see it that way. As Hollander notes: “Actual women take “Fashion” seriously or not, depending on their lives, means and views; but they may all believe that it is something legitimately possible for them, something any woman may ignore if she likes but always has an absolute right to take part in…. Most men, in accordance with modern rules, are still quite comfortable ignoring “Men’s Fashion” in its show-businesslike aspects, and feeling that it is not actually available to them nor really even aimed at them.” And that: “[f]or the past two centuries, men have dreaded looking like fools much more than women have; and so the dress of the male tribe has had a somewhat stronger uniform quality than the female one. Women have envied that very thing about it—and sneered at it too.”

What Hollander overlooks is those of us who want to participate in Fashion—I’ve always been a bit of a metrosexual, decades before the term was coined—but who felt it was off-limits due to their gender. As Helen Boyd’s husband, Betty, put it: “Sometimes I just like pretty shoes and pretty blouses but because I have a penis we have to use big words to describe it.” I’ve often said that if I were a bit braver and society were a bit more accepting I’d be tempted to do the Eddie Izzard look part of the time—someone who dresses as a “man,” but with make-up, painted nails, jewelry, plus some flashier sartorial elements of women’s clothing.

If I’d been able to this when I young, would I have become a crossdresser? Probably. Doing something one knows is stigmatized requires some deep-seated drives, as evidenced by the difficulty that even those of us who hate their crossdressing have giving it up. And I’m well aware of my other reasons—among others, a chance to take a gender role vacation and a chance to be someone else when I was an unhappy, socially awkward kid.

But I do wonder. I’ve heard enough accounts of crossdressers, particularly those who started as young children, where the initial attraction was simply to wear the “pretty things” that girls got to wear. Certainly, there’s an obvious transgressive thrill to wearing what boys/men don’t get to. But to what extent is it simply Fashion’s siren call to wear something other than what one is currently wearing. To use clothing “to be mutable and multiple, decorative and colorful” (as Hollander says of women’s fashion). To participate in what Hollander refers to as the “ancient forms of display—glitter, exposure, constriction, adornment” that were once the prerogative of both genders—and things that many crossdressers seem to adore. To have available the dizzying array of choices seemingly available in women’s clothing. A crossdresser I know refers to herself as a “glamoursexual” and I think that’s not a bad way of putting it. As Hollander notes, a concern about the decorative effects of one’s clothing would never have been despised as effeminate by Henry VIII or any of his contemporaries in Renaissance days.

But I think we avoid acknowledging the importance of fashion and clothing in the reasons why one might crossdress because it’s often considered “nobler” (or at least more “respectable”) to talk about being “feminine” souls trapped in men’s bodies—and because there’s the fear that doing so seems frivolous. Not to mention the whiff of fetishism. Carrie in “Sex and the City” may be allowed to obsess over Manolos, but a man who does so is considered a pervert. And god knows, I have seen crossdressers online whose only topics of conversation seems to be shoes and the heights and styles thereof. Nonetheless, Hollander makes a number of observations about Fashion and its participants that I think provide some very asute—if wholly unintended—insights into the attractions and psychology of crossdressing.

It’s intriguing that the two major feminine innovations in fashion—the skirt (which split off from the dress) and décolletage—are ones that fascinate many crossdressers, especially in tandem with the mini-skirt. There’s an obvious appeal in that these are “women’s only” clothing—men’s fashion has never seriously incorporated either, although its has borrowed many “women’s” elements. (Often this borrowing is actually a bit of sartorial recycling since these were men’s fashions that had been long ago discarded and subsequently adopted by women.)

But equally importantly, they both show off the body in a way that men’s clothing simply doesn’t. As Hollander notes, while men’s fashions clearly articulated their form in ways that women’s fashion didn’t, men’s actual bodies invariably remained fully covered. “Men’s fashion has never used provocative exposure as part of the formal scheme; and shirts, once invisible under medieval doublets became elegant status symbols when they began to emerge, not erotic elements…. Traditionally, a man in nothing but underwear is undignified and ridiculous, or vulnerable and perhaps even sacrificial, but symbolically stripped naked, and not enticingly semi-nude.”

Even today: “Modern men’s short-sleeved formal shirt, often forbidden in strictly correct circumstances, have their disturbing flavor partly because they were really borrowed from women, for whom arm exposure is respectable. Men have allowed themselves to take their shirts off, or to roll up the sleeves and unbutton the collar, in negligent or hearty modes; but they have not been moved to cut open the neckline or cut the sleeves so as to exposure the skin in interesting ways. Nor did they ever do so with coats, gowns and doublets, all during fashion’s long history. Even very short shorts for men, along with skin-exposing undershirt, both quite recently adopted, are also slightly disturbing as public male garments for city wear—I believe because they also have dared to borrow the modern female rule for ordinary exposure.” It’s notable that the opened-a-bit-too-far shirt of the stereotypical lounge lizard in fiction is used to symbolize his sleaziness. In contrast, in antiquity as Hollander notes, “it went the other way: men were bare and women covered.”

So one of the appealing things about crossdressing for me is precisely that ability to be deliciously exposed, to put myself on display in a way that would at best get me labeled an exhibitionist (and more likely a pervert) in masculine dress. And I’m not even talking about slut-wear. Rather it’s just being in something dressy and showing a bit of leg and a bit of neckline, and clothing that follows my (faux) curves. No more than a woman who’s proud of her body might show.

This was brought home to me recently when I attended an event in the sort of formal gown I’d desperately envied as a young man in a tuxedo. The dress was black just as my tuxedos had been—so it was a draw on color—although admittedly black velvet is a far more sensuous fabric, and the bow as well as draped fabric around the neckline provided more ornamentation. But it was the bare arms, chest and back, plus a hint of ankle and most importantly the way the dress gently hugged my body that made me feel profoundly sexy in a way that I’d never felt in a tuxedo, no matter how well tailored.

Hollander says the freeing of women from corsets in the 1920s and 1930s wasn’t fundamentally a matter of practical comfort—women had been doing physically taxing things for centuries in corsets and considered themselves comfortable—rather “[i]t instead concerned a new style of female corporeal pleasure, one more visibly expressive of what women had always like about their own bodies, the physical feel of flexibility and articulation in both limbs and torso, even without vigorous activity, the sense of subtle muscular movement and the strength of bones under smooth skin, the rhythmic shift of weight. Literature and nude art show that men had always admired women’s bodies for these very qualities but during most of European history they were personal secrets only to be privately enjoyed and perhaps revealed by artists, but never openly expressed by fashion itself.” Perhaps crossdressing stems in part a desire to experience for myself what men had traditionally admired about women’s bodies from afar.

Of course, there’s a huge difference between feeling you can put yourself on display and feeling that you’re obligated to do so. En femme, I’m a “big chick” no two ways about it and I can only imagine the pressures I’d feel as an actual woman who has to confront the beauty myth every day. But if women face too much pressure to look sexy, often men lack the opportunity to feel sexy at all. As Hollander says, a man “[w]ith the shirt collar open and the sleeves rolled up, he may indeed be very erotically exposed; but that effect, unlike deliberate feminine décolletage, only succeeds by looking artless.” [Emphasis mine.] So artless in fact, that a man himself would never consider that state of dress sexy. The widespread popularity of lingerie among crossdressers I think is an attempt to evoke that feeling of consciously being “enticingly semi-nude” that they feel isn’t available to them as men.

There’s a similar appeal in our attraction to make-up. Hollander argues that in the 20th century, personal beauty became “a variable individual manner no longer associated only with a perfect young face and figure”—which was emphasized by the growing cosmetics industry, i.e. beauty wasn’t just for adolescents and that “[m]akeup became the emblem of the conscious, creative charm that transcends all indifferent physical attributes, and therefore makes age irrelevant.” Crossdressers also received these messages—even if we weren’t an intended audience and on a practical level, crossdressers that I’ve seen both en homme and en femme typically do look younger and more attractive en femme, since makeup is by definition intended to enhance one’s features. Would I want to feel like I had to do my make-up every morning? Definitely not. But damn, I do feel more attractive when I’m wearing it.

(The pernicious side to this beauty myth is that if you’re not beautiful there’s no one to blame but yourself. It’s the equivalent of the anxieties that American men have felt about being “success objects.” Free to be a “self-made man” (unlike the Old Country where own’s place is society was historically usually inherited and unchangeable) you’re free to succeed—but if you don’t, or aren’t as successful as you feel you ought to be, the “failure” is yours and yours alone. The head of one cosmetics company once said there are no ugly women, only lazy ones—and its interesting that the jab also invokes the same “lack of effort” ascribed to unsuccessful men.)

Obviously putting on make-up is time-consuming, women’s clothing and shoes can be far less physically comfortable than men’s clothing (although men’s clothing, such as ties, aren’t necessary comfortable either). And wigs, breast forms and hip pads are often hot—“trannies in heat” really means being constantly worried an unladylike “glow” (OK, sweating a like a pig) in summer weather. But the psychic comfort crossdressers get often outweighs any physical discomfort—just as it has for any dedicated follower of fashion.

According to Hollander: “Contrary to folklore, most changes are not rebellions against unbearable modes, but against all too bearable ones. Tedium in fashion is much more unbearable than any sort of physical discomfort, which is always an ambiguous matter anyway; a certain amount of trouble and effort is a defining element of dress, as it is of all art. In the past, stiffness, heaviness, constriction, problematic fastenings, precarious adornments and all similar difficulties in clothing would constantly remind privileged men and women that they were highly civilized beings, separated by exacting training, elaborate education and complex responsibilities from simple peons with simple pleasures, burdens and duties. Change in very elegant fashion usually meant exchanging one physical discomfort for another; the comfort of such clothes was in the head, a matter of honor and discipline and the proper maintenance of social degree.”

While the satisfactions for crossdressers are different than those of the privileged men and women of yore, it’s interesting that we often glory in precisely those fussy bits that drive women crazy—and ones that they’ve often abandoned. In “Girlfriend: Men, Women, and Drag” Holly Brubach described how at a famous New York City boutique for drag queens and crossdressers: teddies, garter belts, Merry Widows “and other paraphernalia which, despite the fact that it is now virtually extinct in most women’s wardrobes, is loving perpetuated here as an integral part of the standard-issue femininity kit.”

The drag queens Brubach interviewed often prided themselves on being far better paragons of “femininity” than actual women and in online crossdressers groups one hears complaints at regular intervals about the lack of femininity in the way women dress and act today, and how they too are “better” at portraying woman than most women themselves. (Fortunately, these complaints from come small minority of crossdressers, ones who fail to see the obvious irony of complaining about society’s intolerance of their desire to wear dresses while simultaneously telling women how they “should” dress and behave.)

But male admirers of transsexuals and crossdressers (less charitably referred to as “tranny chasers”) do often comment about how we’re more “feminine” than the real thing. Which in a sense is probably true since we have to try harder to be seen as “women.” And so doing convincingly can be tremendously satisfying. Not only in the sense one might (or might not) feel in inhabiting one’s “true” gender—but also in the sense of accomplishment, of mastery of craft.

Hollander points out that being good at Fashion is also hard work. “With all the contradictory pressure at work in Fashion, it’s clear that those who are the best dressed are those with the greatest degree of self-knowledge, whatever the fashion genre…. [T]his brand of self-knowledge is usually not consciously and therefore arguably not knowledge at all, and it effects are only another kind of unconscious revelation. To seek it consciously means to devote time and effort to specifically visual self-understanding, not to physical or moral improvement. It means deep detached study in multiple mirrors, the sort of private workout that yield real knowledge of your actual appearance: your rear views and side views, both sitting and walking, your normal head movements, your gestures and facial habits while speaking—all requiring a detailed self-regard that has itself gone out of fashion, again especially in puritan America. It is the sort of thing associated with expensive French courtesans or English Regency dandies whose only assets were their distinctive physical charms, which required constant technical maintenance backed up by ferociously clinical self-scrutiny.” Or of crossdressers whose frequent obsession with mirrors and photos is well known.

Not that narcissism (and sometimes self-arousal) isn’t a factor in our love for own images. But even if we’re considerably less self-aware than the courtesans and dandies about what we’re up to, I think some of the same self-scrutiny is at work. To paraphase Fecility Huffman, we have to learn “feminine attractiveness” like a second language. So I for one have carefully studied my photos figuring out which angles and which poses are most flattering. Consequently, I’m far prettier in them than I appear in real life.

Crossdressing may be pleasurable, but it’s also a skill that one can take pride in when done well. A reporter for a gay magazine who went out for an evening en femme with a local crossdresser’s group aptly summed it up in his story: “A successful transformation involves more than slapping on powder and lipstick, throwing on a dress, and talking in a falsetto. As a creative art form, crossdressing can be as demanding and expressive as painting or sculpting, singing or acting.” Or Fashion.

For what it’s worth, crossdressing is quite common, about 5%-10% of men do it on a regular basis, and many more have experimented with it at some time or another.

It’s important to remember that his dressing has nothing to do with you — don’t worry that you’re not “not enough of a woman” for him, etc. It’s something he’s probably done since childhood and will continue doing for the rest of his life whether or not you’re with
him. The fact that he was willing to purge has everything to do with you — his love and devotion to you and he desire not to lose you.

Unfortunately, as you’ve discovered society has a lot preconceptions about crossdressing, which are almost entirely wrong. The vast majority of crossdressers are straight. Researchers have clearly established that sexuality and gender role identity are two
distinct things.

The reasons why we dress are many and varied, and are different from individual to individual. But there’s a couple main reasons. One is we like to look pretty and feel sexy in a way that’s allowed for women, but not really allowed for men. Another is to express a side of ourselves that society as deemed “feminine” (this is probably especially true of guys who are macho or Spock-like en homme, as many crossdressers seem to be). And it also can be an escape, both from the everyday pressure of life and the specific pressures of having to prove your manhood on a daily basis. (It’s pretty well documented that stress is
a common trigger for dressing.) In that sense dressing isn’t that different than putting on a Starfleet uniform for the chance to be someone else for awhile. But like any “grass is greener” envy, crossdressers don’t necessarily have an accurate view of what a woman’s life is really like. Often the way we dress and act probably has more to do with what we’re repressing than our actual view of women.

Because sexism is still all too present in our culture, it’s acceptable for women to act “masculine” (up to a point, of course), while men who want to emulate women are traitors to our gender for giving up the “male priviledge.” That makes a lot of people — male
and female — uncomfortable. And crossdressing also causes people confront their own stereotypes about what’s appropriate behavior — as well as the unconscious discomfort they may have with gender roles. All of these may be reasons why your friends think you’re strange to stay with your fiance. The irony of course is that many crossdressers while en femme display exactly the sort of sensitive qualities women keep saying they
want in a man.

I can understand how you feel isolated. Believe me, we understand. It’s possible with more education your friends may become more understanding. It’s possible, they may not. Probably a lot depends on their background and how rigidly they view gender roles. The good news is that there are good online communities where we crossdressers can listen and try to explain things from our perspective. There are also a number of SOs in various online forums — some accepting, some struggling with acceptance — who can do
the same. One them wrote a useful article about the “acceptance pendulum” many SOs go
through.

I know you’re struggling with this, but your SO is lucky to have someone as loving and accepting as you.

But I think discomfort with gender roles plays a bit part of it. I seem to remember some studies indicating a good percentage of men and women have personalities that fall outside the accepted norms for “masculine” and “feminine” personalities. It’s interesting to me that
there seem to be a lot of crossdressers from conservative social environments, where gender roles are typically more rigid, as well as the number of folks engaged in “logical/rational” profession, i.e. engineering, programming, etc. For the former group, “becoming” a woman may be a way to express aspects of their personalities that aren’t socially accept as a man. For the latter, I think crossdressing is a way of letting out the non-rational parts of their personalities that they normally keep in check. (It’s interesting that engineers, programmers, etc. are often over-represented in other “alternative” activities from the Rennaissance Faire to Burning Man, to Trekking, where they also have a
chance to become someone else.)

Lately, I’ve become intrigued by the question of why there are so few female crossdressers (although crossdressing play is more prominent in the lesbian community) when there are a good number of MTF transsexuals, especially if you factor in the stone butches and other strongly butch lesbians who to my outside eye often seem like they’re exhibiting transgender-ish behavior. The obvious answer is the greater flexibility in clothing, but that
ignores the fact that it’s intent that makes it crossdressing rather just wearing clothes of the opposite sex.

There’s an interesting female parallel to cross-dressing: tomboyism. From the research I’ve run across there’s two types of tomboyism, the first and widely common is “expansive” (i.e. wanting to play with dolls and trucks), while a minority of tomboys reject female behavior and sometimes even deny they’re girls. Lesbians (especially butches) have a much higher likelihood than “normal” of having been tomboys, especially the second type. But interestingly, bisexual women, who self-identified as andrgynous at suprisingly high rates,
had a strong likelihood of recalling being tomboys part of the time. Raven Kaldera, a transman, mentions having seen some female crossdressers and says they typically begin in their 20s. (Unfortunately, he doesn’t mention if any of them were tomboys, so I don’t know if it’s a resumption of behavior or something new. But my suspicion is the later
onset is because when the social pressures that typically put an end to tomboyism are weaker.)

The sum of this suggests to me that there’s a number of women who’ve got similar gender discomfort to us MTF crossdressers (at varying levels). Things do get murky because discomfort with gender role has been the focus of feminism, whereas with men there’s really not been a widespread equivalent. Women with gender role discomfort turn to feminism, where men with gender role discomfort may turn to crossdressing. Another factor is that MTF presentation involves “dressing up” whereas “masculine” women
generally are “dressing down” (short hair, not wear much, if any make-up, “practical” clothes, etc.) And of course the great range of acceptable clothing for women. So MTF crossdressing involves an overt awareness of what you’re doing, whereas women don’t necessarily have to been as self-aware, as in fact probably see it more as “not being
girly” than “being masculine.”