'A woman must not wear men's clothing, nor a man wear women's clothing,
for the Lord your God detests anyone who does this.'
- Deuteronomy, 22: 5
Really? I mean what's the problem here: why is God so troubled by everything?
I suppose it's because the simple pleasure of cross-dressing creates an element of uncertainty and causes the poles of male and female to vacillate via an abolition of differential opposition.
Cross-dressing demonstrates how the signs of sex can easily be separated from biology. In other words, it reveals gender and sexual identity to be nothing but a playful and performative game involving clothes, hair and cosmetics; a question of style, rather than a fateful combination of anatomical fact and metaphysical essence.
Personally, I have always found something enchanting about 'men dressed as women' and 'women dressed as men'. Like Wilde, I am of the view that wherever there is loveliness of appearance, then there is no fraudulence.
And besides, as Judith Butler points out: we are all transvestites.