Cross Dressing

As this 1935 picture of Katharine Hepburn proves, a male jacket and trousers on a woman is one of the sexiest looks around. Chanel always borrowed her lovers' sweaters and sports coats, and any man who has ever been deeply, madly, physically in love with a woman knows the sexual thrill of seeing her wearing an item of his kit, even if it is just his old school cricket sweater.
There is nothing new about cross-dressing. Travesty, as it is correctly called, goes back to before the 17th century. But whereas men in women's dress alarmed church and state, women wearing men's dress were seen as merely having the impertinence of an inferior sex.
The high-minded Victorians found male impersonation rather worrying, while loving the frisson of saucy music-hall stars who, dressed in men's clothes, had much more freedom to sing songs laden with naughty double entendres. The showbiz tradition grew with Hollywood movie stars such as Marlene Dietrich, Judy Garland and even Julie Andrews doing some of their most impressive work looking glamorous in top hat and tails.
And it is true that men's clothing on women never goes out of fashion. Most designers love the androgyny of oversize - which is what normally happens when women borrow bits out of men's wardrobes - but it isn't just top designers who can do this. Any woman in love can nick something from her man and look terrific in it. Just one caveat, though: if you are larger than he is, resist. The look is Artful Dodger cheeky, not Billy Bunter squeezed.

First published 2003