I've ridden bareback in skirts before. I don't like wearing them with a saddle though, because I fear that something will get caught if I fall and I'll get dragged. Also, chafing...Ouch... Yeah. I'm just going to stick with bareback.
A couple of girls that used my horses for a parade wore skirts, and they rode astride. Their skirts were very long and covered most of the rump behind the saddle. I don't know anyone that does it a lot though, I think it gets in the way more than anything.
I just got married and I wore this BEAUTIFUL dress. It was extremely long and I honestly had some troubles walking on it. I wanted to have pictures with my horse but my mom(she bought my dress) told me I wasn't allowed to wear it with my horse cause I would ruin it and she isn't tall enough...she would trip as well...here is a picture of my dress.
The first one was takin by my husband's mom and the last one was taken by my friend :)
Thanks for asking this! I want to ride bareback for some photos in a long flouncy skirt and was wondering about the level of weird glances I'd get, lol! You could wear pants or something underneath to make you more comfortable if it's real riding riding and not just posing.