I didn't have any trouble riding in a skort. It felt weird at first, but I got used to the flapping behind me. I agree with Denise; I would rather buy the unpadded wrapper to put on over shorts if i ever was in a place where I felt uncomfortable in shorts. So far, that has only happened once, in Edgartown, on Martha's Vineyard, though I'm pretty sure the people were staring more at my husband's shorts, matching jersey, socks, and sandals, rather than mine.