Crossdressing and Fashion (with a capital "F")

(by Marlena Dahlstrom)
“It’s not the clothes.” How many times have I said that when the lament of “women wear pants, so why can’t I wear a dress” surfaces with clockwork regularity on online crossdressers’ groups I belong to. Usually it’s in the context of making the what-ought-to-be-obvious point that women wearing men’s-styled clothing aren’t trying to portray themselves as the opposite gender, as crossdressers typically do. And yet, after reading Anne Hollander’s fascinating “Sex and Suits,” which looks at the evolution of modern men’s and women’s clothing, I wonder just how much of my crossdressing is in fact about the clothes.

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: “For 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 (warning: site has audio clips) 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.