Cross-dressing (and here i refer particularly to men dressing up as women) has tended to have a bad reputation. The idea of a man taking pleasure in putting on women’s dress has traditionally been seen as laughable, pitiful – and plain sinister.
It was usually assumed that a marriage would almost certainly break up the day a wife found her husband in her underwear; From this perspective, cross-dressing seems like an admission of failure. Instead of living up to an ideal of strength, ruggedness and sheer ‘normality’, a man keen to slip on a dress is taken to be a deviant of a particularly alarming sort.
But in truth, cross-dressing is grounded in a highly logical and universal desire: the wish to be, for a time, the gender one admires, is excited by – and perhaps loves. Dressing like a woman is merely a dramatic, yet essentially reasonable, way of getting closer to the experiences of the sex one is profoundly curious about – and yet has been (somewhat arbitrarily) barred from. We know cross-dressing well enough in other areas of life and there think nothing of it.