A cross to bear

Heterosexual men wearing women's clothes - our last taboo

Some years ago, I had cause to investigate the subject of cross-dressing, specifically heterosexual men who dressed up in women's clothing. This is our last sartorial taboo. We have long ceased to think - in this country at least - that there is anything wrong with women wearing trousers. You can pretty much go out wearing anything and you'll merit little more than a look and a comment. But just mention the subject of cross-dressing and you have an entire evening's conversation stretched out before you.

Cross-dressing and transvestism are often confused, erroneously, with signs of homosexuality. While some gay men do dress in women's clothing, that is generally more in drag situations and for entirely different reasons. The men I spoke to were touchingly honest, but they all had one thing in common, which was a fascination with their mother's clothing. One man, with whom I had a correspondence for several years, told me about how he had become obsessed with his mother's stockings and, as a grown man doing military service in the 1950s, he had worn fully fashioned seamed stockings under his uniform. That takes a special sort of courage. He did much to help me understand why men "did it", although he was so afraid of his identity being uncovered, I would have to write to him via a holding address in California and he only ever signed his letters "JL". What he told me was that, in his experience, cross-dressing had nothing to do with wanting to be a woman, but everything to do with women's clothes being forbidden to men and, also, with wanting to be closer to women. The touch and feel of women's clothing was particularly important.

No matter what each man's story or what his particular "fetish" (I use the term loosely), the fear of being found out was always paramount. One told me about how, as a young boy, he had tried on some of his aunt's mascara, which then wouldn't come off (anyone reading this, if you don't have eye make-up remover try baby oil or any other oil), so he cut off his eyelashes. Another cut into his nails with a razor blade to try to get nail varnish off.

Once the personal histories were out of the way, many relished simply being able to talk about fashion - often the first time they were able to do so openly. "If you're a heterosexual man of a certain age, you just don't feel you can talk about 'what's in' for any length of time, but I long to talk about the latest heel height [on women's shoes]. I long to be part of that chit-chat."

And what's really interesting is that, despite knowing all this, and reassuring women over the years that it's fine for their husbands to try on their dresses every now and again, I still would feel distinctly uneasy if my own partner did it. Why?

Annalisa Barbieri was in fashion PR for five years before going to the Observer to be fashion assistant. She has worked for the Evening Standard and the Times and was one of the fashion editors on the Independent on Sunday for five years, where she wrote the Dear Annie column. She was fishing correspondent of the Independent from 1997-2004.

This article first appeared in the 12 May 2008 issue of the New Statesman, 1968 The year that changed everything