The roots of sidesaddle riding are hundreds of years old, although the riding technique is restricted primarily to women riders. In European tradition, although women rode horses, it was considered improper for them to ride astride. As early at the 11th century, women rode in specially designed sidesaddles which resembled armchairs, with a wooden plank to rest their feet on. These saddles were probably lacking in safety, and the design was refined in the 15th century to make riding both more comfortable and more safe. The design has changed little since then, although most modern equestriennes prefer to ride astride, because of the safety issue.

A side saddle has two pommels, one oriented slightly off center, and another below it. Traditionally, a side saddle is designed to for riders to sit on the left hand side of the horse, although either side is technically correct. The top pommel is also known as the horn and the rider swings his or her top leg over the horn, while the lower leg is tucked under the leaping horn, or second pommel, which is curved to enclose the top of the leg. The lower leg is placed into a stirrup, and the rider is ready to ride.

Learning to ride side saddle takes some training in riding technique. The rider must carry a whip to use on the off side of the horse for cues, and must also learn to hold a balanced, even seat. The horse must also be trained to carry a side saddle rider, as the off centered weight can be a strange sensation for a horse accustomed to more conventional riding. The fit of the saddle to horse and rider is also very important, as an improperly fitted sidesaddle can resort in saddle sores and other discomfort for both parties.

Although women are no longer expected to ride side saddle, some riding organisations exist to promote side saddle riding and many horse shows offer a side saddle class or allow side saddle riders to compete in regular classes. A skilled side saddle rider can hunt, jump, and practice dressage with ease, often to the amazement of conventionally trained riders. Side saddle riders also tend to wear a traditional riding habit, which consists of a full apron to cover the riding jodhphurs worn underneath. The apron is not actually a full skirt, but it is designed to look like one until the rider dismounts, at which point the open back will become apparent.