I haven't done riding in a skirt, I feel uncomfortable with it. Especially when a wind blew so hard that it could make my skirt flew. Also, it could get you into an accident. But I think it depends on you, if you're comfortable with it, wear it. but for me, I'm not comfortable on wearing skirt while riding a bicycle. It makes me conscious especially when people look at me. I felt that some of my underneath garment is showing off or maybe they're waiting for it to show.