Most Helpful Guy
You go up and down, grinding your legs on the saddle and (sweaty) horse.
Wear a horse riding pants or a decent tough jeans.
Also wear shoes with a gap. Like hiking boots or riding boots.
No flat bottom cause it can slip thrue the "feetholders" (idk the English word) and that might fuck you up when you fall. Cause you would hang next to the horse.
Most Helpful Girl
Riding horses in a dress? I think it would be more comfortable to ride in an outfit like in the pic below. Riding breeches plus boots in case you step in mud, and a matching belt to cinch the whole outfit together, really cute!