| Field | Transportation or Sport |
| Went Obsolete | Most aside riding stopped in the 1920s, but the skill never went completely obsolete |
| Made Obsolete By | Acceptance of women riding men's saddles |
| Knowledge Assumed | Basic horsemanship |
| When useful | When riding in a skirt, or riding by a person with leg injuries or handicaps |
Aside riding can be traced back to ancient times. At first, women used men's saddles with a footrest. These early sidesaddles were mostly used by nobility for ceremonial display; women in the Middle Ages also rode astride (like a man.) Even as late as the 18th century, some notable women rode like men. Yet by the mid-19th century, respectable women were expected to wear a riding habit (skirt and top) and ride sidesaddle. This continued until the 1880s, when the advent of the bicycle once again introduced the idea of a woman wearing a divided skirt or bloomers in public. By the 1920s, a woman wearing riding breeches and riding aside was accepted in most circles, and the sidesaddle became a thing of the past.
Sidesaddle riding styles varied according to the type of sidesaddle. Most 19th century and “modern” sidesaddles have two horns, usually located on the left side of the pommel (front of the saddle.) One of these horns did not move, the other, which was curved, rotated. This lower horn was called the “leaping horn” and enabled women to jump and ride spirited horses more easily.
When riding aside, the rider's right leg rested on top of the upper horn. The leaping horn rotated so that it fit over the top of her thigh, and her left foot rested in the stirrup. In an emergency, the women could raise her left leg, thus gripping the saddle.
The danger in aside riding was not that a woman might fall, although it was possible. The main dangers were that she might catch her skirt on the horns if she tried to jump free and be dragged, or that she might pull a rearing horse on top of her.
Aside riding had its difficulities. The aside rider had to be skillful, or she could damage her horse's back by putting too much weight on one side. The sidesaddle itself was also relatively expensive and had to have periodic restuffing to make it sit straight on the horse. The aside rider sometimes needed the help of one or more grooms to gain her seat, as she had to manage her extremely (at times) long skirt.
Yet women who grew up riding sidesaddle sometimes preferred it. Since it did not require the muscular leg strength that riding a man's English saddle required, women could ride and even hunt aside into their later years.
Since the 1970s, aside riding has made a comeback, and many women are learning to ride aside. Modern saddles and the development of the apron skirt (a sort of half-skirt that covers only the left side and front of the legs) have made aside riding safer.
