Skirting the issue

Grayson Perry resplendent in purple satin. Eddie Izzard sexy in black leather. Is transvestism still taboo, or are men in dresses the future of fashion? John Walsh explores the allure of guys in gowns

In the long and spectacular history of odd behaviour at award ceremonies, Grayson Perry's appearance on stage at the 2003 Turner prize may not have been up there with the real titans of embarrassment (Halle Berry in hysterics, Gwyneth Paltrow in floods and Björk in her swan outfit at the Oscars, Graham Chapman of Monty Python fame crawling all the way across the dining-room floor and up the stairs at the Bafta awards), but it was still pretty out there. To receive his prize, Perry wore a fetching lilac satin dress with a lime-green collar and bow, a size-18 version of a little girl's party dress patterned with bunnies and hearts and the word "sissy". If the Shirley Temple of Wee Willie Winkie were to be transformed into a 43-year-old potter from Essex, she might choose just such an outfit in which to stand before the company and sing: "I've written a letter to Daddy/ His address is heaven above".

It was just a tiny bit creepy, which was exactly what Perry intended. "One of the reasons I dress up as a woman is my low self-esteem," he told the press, "to go with the image of women being seen as second class. It's like pottery. That's seen as a second-class thing too." But more immediately curious was the oddness of the family trio who were snapped for the camera: Grayson, his wife Philippa and their daughter Flo. The oddness lay in their utterly sweet, every-day ordinariness.

Philippa beamed and glowed in a red bustier and black ribbon choker; Flo was a typical 12-year-old in a skull-and-crossbones T-shirt. They clasped hands and smiled and hugged each other as if the large man in their midst were not wearing the kind of costume you associate with paedophile fantasies, and a ginger fright-wig. They looked as if Grayson dressing up as his craftsman alter ego "Claire" were the most natural thing in the world. The family portrait that appeared everywhere on Monday morning dared the news-reading public to condemn or laugh at Perry as a sicko, a perv or a card-carrying prat.

Can it be that cross-dressing is becoming acceptable as a style choice? Men who habitually dress in women's clothing can be called "transvestites", as if they were members of a sect, followers of an "ism". If they wear women's clothes temporarily (come in, David Beckham in his Polynesian sarong and his wife's knickers) we call it "cross-dressing", implying that they don't really mean it, they're having a laugh, they're winding up the more bourgeois-minded of their peers. But the distinctions are getting blurred. They day may be coming, gentle (male) reader, when Saturday night may find you sliding your manly frame into a pencil skirt and 15-denier stockings just because you fancy going out in something different.

Take Eddie Izzard, the nation's favourite TV (that's transvestite to you and me). Izzard is an original comedian in that, while he dresses on-stage in women's clothing, like thousands of drag acts before him, from Old Mother Riley and Danny La Rue to Lily Savage, he doesn't tell jokes in character. Looking exactly like a hefty bloke in fishnets and a hundredweight of foundation powder on his manly chin, he wanders the stage telling jokes about Daleks and monkeys stranded in trees. He does not bang on about female troubles, or pretend to be someone called "Claire". Where female impersonators used to dress in huge ballgowns and wigs to resemble Southern belles or Tammy Wynette, Izzard squishes himself into tight black PVC minis or Paisley-print skirts from Topshop, as if to assure us that transvestites also have a cupboard full of everyday wear for when you feel like popping down to Sainsbury's.

Pop stars have enjoyed a long flirtation with cross-dressing, starting with Mick Jagger's astonishing white moiré minidress (designed by Michael Fish) at the 1969 Rolling Stones concert in Hyde Park, where he released hundreds of butterflies and recited "Adonais" for the recently deceased Brian Jones. The minidress seemed just a typically Sixties piece of cultural appropriation, as familiar but surreal as the ascending lepidopterae and the Shelley poem. Two years later, David Bowie posed in another Fish frock for the cover of The Man Who Sold the World, lying on a couch, scratching his head, as if wondering why he's woken up dressed as Lauren Bacall. "You must understand," Bowie said, "that it's not a woman's dress. It's a man's dress. The important fact is that I don't have to drag up. I'm just a cosmic yob, I suppose. I've always worn my own style of clothes. I design them. I just don't like the clothes that you buy in shops. I don't wear dresses all the time, either. I change every day. I'm not outrageous. I'm David Bowie."

In the last two decades, countless others have joined in: not just Boy George in his rag-doll smock and Malcolm McLaren in his bondage tartan skirt, but Keith Flint from The Prodigy, the strikingly non-camp Evan Dando of the Lemonheads, and the doomed and extremely un-skittish Kurt Cobain of Nirvana. It was a cross-dressing wave of manly rockers, and it might have changed all our habits of personal display, had it not been for one man: Kevin Rowland of Dexys Midnight Runners. He showed up at the Reading festival in 1999, balding and inelegantly wasted, and sang some numbers dressed in a rather graceful white satin shift. Nothing wrong with that, but he accessorised it with a pair of white stay-up stockings with frilly tops, and unspeakable acres of naked thigh. Sophisticated male fans, well used to their quondam hero's excesses, could barely quell a desire to be violently sick.

The focus of the cross-dressing debate was the Men in Skirts exhibition that opened last month at the Metropolitan Museum of Art in New York. It was attended by the male corset-wearing classes en masse, from Eddie Izzard onward. Its profuse displays of photographs and designs, the organisers claimed, "dispel the myth that the skirt is an exclusively female garment. It looks at contemporary designs inspired by togas, frock coats, kilts, dhotis, sarongs and kaftans - all items traditionally worn by men". The accompanying book of illustrations (published by the V&A museum) offers a brisk tour d'horizon of skirts in the classical world, from the floor-length chiton, worn by tough Delphic charioteers, to the curiously fetishistic little number - the pteryges, or the row of long leather straps attached to the bottom of the Roman soldier's vest that dangled fetchingly down to mid-thigh. They show how the classic look adopted by Henry VIII for portraits is a combination of a short, loose gown and a full-skirted jerkin with long tight stockings underneath - disconcerting for those who think that the current girlish fad for combined jeans-and-skirt is terribly cutting-edge and funky. They track through the noisome rise of the full-cut "petticoat breeches" that were all the rage in the 1660s and made gentlemen at court look as though they had settled a gigantic pumpkin around their thighs.

An Oxford antiquary called Anthony Wood commended in appalled tones in 1663 that it was "a strange effeminate age when men strive to imitate women in their apparel, viz long periwigs, patches in their faces, painting, short wide breeches like petticoats, muffs, and their clothes highly scented, bedecked with ribbons of all colours". Well, well. Plus ça change. We haven't quite reached the hermaphroditic levels of the mid-17th century, but we may be getting there.

The point about cross-dressing is, of course, its exclusivity to the famous, extravagant and exotic. Just as there's no evidence that the average peasant tilling the fields of Gloucestershire showed any interest in dressing like Robert Dudley, Earl of Leicester, in his ludicrous petticoat breeches, so there's no immediate sign of the high street shops - Gap and Woodhouse and Reiss - filling their shelves with Bowie-esque "men's dresses", nor even with Jean Paul Gaultier kilts, the most acceptable form of male be-skirtedness, as modelled by Ewan McGregor, Robbie Williams and Samuel L Jackson in the film The 51st State. It will take more than a footballer's sarongs, pop kilts and artistic party-frocks to persuade British men to venture through Peckham High Street in a heliotrope ballgown from Monsoon, no matter how fashionable, no matter how fetchingly it clings to their silk stockings.

It's a chap thing. We've spent a thousand years getting things wrong in day-to-day dress, perpetrating heinous fashion crimes, and being sniggered at for our pains by our womenfolk. Trying to imagine one's future self, clad in plunging Vivienne Westwood and Dior stilettos, being pitilessly scrutinised by one's daughters, is a prospect to freeze the blood.

Legs & Co: how fashion is taking its trousers off

In the world of designer fashion, almost anything goes. But one of the last great taboos is the male skirt. Kilts, of course, aren't shocking enough for designers. Worn for novelty and impact, rather than as transvestism, the male skirt has a chequered history.

Various designers have attempted to tempt men out of their trousers, not least because a male model in a non-bifurcated garment will guarantee instant press coverage. Among these designers are some of fashion's greatest names - Vivienne Westwood, Giorgio Armani and Kenzo. Genius shock merchant Jean Paul Gaultier has long couched his menswear designs in references to sarongs, saris and dhotis. These traditional Asian garments somehow nullify any threat to masculinity; David Beckham almost managed to pull off the sarong look. Other names have recently joined the fray. In January, the first delivery of Yohji Yamamoto's sleek, entirely black take on the man skirt will hit the stores. Last year the V&A in London held an exhibition, Men In Skirts, entirely devoted to the controversial subject. However, the males employed by fashion designers to model these garments are tall and slim, with legs that most women would kill for. They look in touch with their feminine side without looking like sissies. What man in his right mind would dare try to replicate the look?

But it is rock stars who have flirted more successfully with the more obviously feminine skirt or dress as a statement of rebellion. Mick Jagger, David Bowie and Kurt Cobain all donned pretty frocks without harming their pin-up status.

In one sense at least fashion is preoccupied with our proclivity for cross-dressing. Next summer, one of the biggest trends will be the masculine tuxedo trousersuit - for women. For the moment, men can keep their draughty skirts.

By Susie Rushton