When the bicycle first appeared, in the 1860's, there was a huge debate on the "appropriateness" of women riding bikes. I saw an interesting exhibit about it in Coventry Transport Museum. To the upper-class Victorians who could afford bikes, the idea of women wearing more practical clothing ("rational clothing", they called it at the time) was scandalous, and there was significant resistance to women being allowed to put on trousers and ride bikes around.
I can't help but feel it wasn't really about clothes, though. A bike is an amazingly liberating thing. What these women's fathers and husbands were really frightened of was women having a certain amount of autonomy, being able to leave the house as and when they pleased. Biking is something you do alone; a woman who owned a bicycle was therefore someone who had the means and capacity to decide where and when she wanted to go by herself.
Today, the issue of clothing still seems to represent a barrier to many women cyclists. I have heard many female friends say that its impractical to take a bike when you're wearing a skirt, that their clothes will get covered in oil, that they're not wearing the right shoes. Personally, I find myself able to adapt to most clothing and don't choose specific clothes to wear when I'm biking. But perhaps that's helped by the fact I don't wear heels. But I actually quite like cycling in long skirts, which leads me to wonder what the Victorians' problem was. Short skirts present more of a problem; but a good solution is shorts underneath, to avoid having to check that your skirt hasn't blown up every five seconds!
Like in Victorian times, clothing issues still seem to prevent women from cycling. Yet just like 150 years ago, it's not really about clothes. There are deeper, more insidious issues at play about the way society views female cyclists. Somewhere along the way, women (more than men, the statistics suggest) pick up that cycling isn't right for them. We should fight this misconception vigorously like the women who demanded their rights when the bicycle was born.