Laura Lipton

^^ Laura Lipton, a seriously accomplished crossdresser, walks down a street in central Paris

What is it about crossdressing that animates in every culture or society I am aware of, today in particular but also back through much history ? What is it ? What moves those who do it, to do it ? I refer here not to entertainments, though much of what I am about to opine applies to those who use crossdress to amuse, make money, or otherwise perplex one’s attention. What fascinates me is those crossdressers who dress for ordinary life in ordinary (though not so ordinary, actually — the crossdresser whom I have in mind dresses smartly and with great care) clothing and makeup. Why do they do it ? How did the ide of crossdressing come to them ? Here one finds every sort of personal recall, reason, and inspiration, because people are different even when they do the same thing. These engage one’s heart as a fellow human, but I am much more interested in the pleasure that crossdressers get — and that they give to those who like to see it. I am no psychologist and approach this subject the way I approach all art : as a lover of beauty.

When I think the noun “beauty” I think always of John Keats and “Ode Upon a Grecian urn,” in which he marvels at the living immortalized by the artist who crafted it 2400 years before. Summing up what the figures and actions on the urn meant to him, Keats wrote, in the voice of the urn itself, “Beauty is truth, truth beauty — that is all ye know on earth, and all ye need to know.” Those words stick to my soul. They urge me to love the beautiful and rely on the truth in it. Hard to parse a more optimistic message ! Yet even as beauty is our doorway into the house of truth, it is, for Keats something more, it is the path of immortality. As he wrote just before the sentence I quoted : “when old age shall this generation waste, Thou doth remain, in midst of other woe Than ours…”


“when old age shall this generation waste” –there you have it. Beauty within us may brighten the skies of a society for a while, but the beauty in art knows no death. It conquers what another poet, Dylan Thomas, called “the dying of the light.” It defats doubt,. It withstands and triumphs and, says Keats, bestows divine meaning upon our otherwise wasting life. To who among us would such beauty not endear ?

And so to the art of crossdressing, which, I must say, proudly actually, has ben a passion in my own life for many decades. As a kid I had no idea why i wanted to do it. I doubt many crossdressers even as adults know why they love to do it. Yet is it not likely that profound love of beauty is a key ? Many societies accord women a second place, and even those in which women enjoy more or less equality in the business of living sometimes devalue women’s worth. yet almost none of us think women anything less than beautiful, attractive, loveable. And if imitation is, as Oscar Wilde said, the sincerest form of flattery, then the serious crossdresser is as sincere as it gets. And I think that this desire to be beautiful, to feel “girly,” and to feel what it is like to be beautiful, is, if not the whole story — of no human activity do we know the whole story — a very, very important part of why crossdressers crossdress.

Let us remember that even in our own supposedly “liberated’ society, and almost tragically repressive in others, there are crossdressers crossdressing. In some societies for a man to dress as a woman is beyond the pale and actually dangerous yet they do it. In Lebanon, in Egypt, In Pakistan, in Russia, in China, in Mongolia and probably in Iran too. You name the country, there are crossdressers there crossdressing despite. This is the power of the beautiful. This is the power that it holds over some men.

Sophie, bambi, Ophelia

By beauty I do not necessarily mean pleasure. Women’s clothes are not always easy to wear. High heels hurt to walk in. Most women’s clothes fit close on the body (which is what fashionistas have in mind when they call themselves “pulled together”). After a full day out one wants to take off the art and just let the body go, artlessly free. (Though pretty soon the desire to be girly rushes back upon one, and one gets dressed again.) Doing one’s make up takes a ton of time and an almost snivelling attention to detail. Yet crossdressers do it — most of us love doing makeup. it validates our passion. It is the magic of our transformation. And maybe that’s it, the transformative : if beauty is like nothing else — which is my entire point in this article — then whoever you are — women too — if you are make yourself a thing of beauty, you TRANSFORM. Of course girls learn the transformative from early on; boys do not. Yet some boys take to it anyway. Despite rejection by family and or friends. despite the threat of taunting and worse by classmates were they to “find out.” In spite of all, boys who take to crossdressing DO IT. In almost every society — which fact offers some powerful proof that beauty is a universal.

Which is my final point. Keats writes that beauty is truth, truth beauty. He EQUATES the two. With no qualifications of time or place — and as I have shown, crossdressers prove it. They exist in every phase of history and almost everywhere. Indeed, it would take an oppression even more totalitarian than Stalin’s to repress crossdressing out of existence., At last, beauty cannot be denied, will not. Any more than what he think of as “true’ can be denied. As Spock would say, it’s not logical. We also today talk of “my truth.’ I find the phrase peculiar and self-centered and a shutting out of one person by another; yet one can say about the serious crossdresser that he is acting out his truth.

Fortunately for all of us, the truth that a crossdresser acts out is no mere theory. Crossdressers are as real as it gets, as significant, and, yes, as beautiful. Pleasing to the eye and, hopefully, to the soul.

Many will also tell you that it’s just fun to do. That I will “dress the ay i want.” That there is no deeper meaning in dressing in women’s clothes. I can’t dispute anyone who says this. Life isn’t always (usually ?) lived to consciously held ideal. Yet even if cross dressing is fun — which it is– and even if doing it is to act the rebel (which it is — David Bowie caught that d rift back in 1973’s “Rebel Rebel”), I’d submit that it is not ONLY fun or an act of rebellion. I am amaze, too, by the numbers of guys who have just begun to cross dress, within the past five years or even the past year, and become part of a truly momentous instagram community of guys dressing up as girls and doing so with fashion skills, make up cleverness, and a ready hand for insightful and playful photo-post captions. These are almost all “straight” guys, many of them married to supportive wives; I’ve seen several instagram [photos of crossdressers and their wives and even some with the kids. can cross dressing be a family adventure ? Seems it can.

— Mike Freedberg / Here and Sphere

WRITER’s NOTE : the photos I have collaged come from friends on Instagram, a crossdressers’ community like no other. The photos shown are a mere selection, even an unfair one. But the level of beauty flaunted here is no rarity. I could just as easily have chosen 8 different people, or 16, or 60, to flaunt upon this column.


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