A female character is labeled as more feminine for riding sidesaddle or showing off her tomboyishness by riding astride.

Sidesaddle riding (also known as riding aside) for women dates back to antiquity. Whether to accommodate women's clothing or because straddling a horse was seen as immodest, the sidesaddle has long been associated with femininity. It makes riding and controlling the horse more difficult with the most extreme examples not allowing the rider to control the horse at all and relying completely on others to guide it. In addition, it is far more uncomfortable than riding astride and this limits the speed the horse can go. Sidesaddles eventually evolved to give the rider control, with the leaping horn sidesaddle giving women the ability to do full gallops and jumps, but the image of the sidesaddle as a serious detriment to horsemanship remained.