Here’s to Maggie Gyllenhaal, cycling through Hysteria (the movie) in full Gibson Girl skirts and petticoats. Her bike is equipped with a wheel cover to prevent her skirt from catching.
The bike share program sponsored by Citi in NYC has thoughtfully put guards over the tires so you can cycle them in a skirt without worry.
I did see women cycling to work in their pencil skirts when I was in Manhattan the other day. I’d have taken a photo, but they were cycling and I was driving (or attempting to), so they zipped past too quickly.