Sidesaddle riding is a form of equestrianism that uses a type of saddle which allows riders, generally female, to sit aside rather than astride an equine. Sitting aside dates back to antiquity and developed in European countries in the Middle Ages as a way for women in skirts to ride a horse in a modest fashion while also wearing fine clothing. It has retained a specialty niche even in the modern world.

A saddle is a supportive structure for a rider of an animal, fastened to an animal's back by a girth. The most common type is equestrian. However, specialized saddles have been created for oxen, camels and other animals. It is not known precisely when riders first began to use some sort of padding or protection, but a blanket attached by some form of surcingle or girth was probably the first "saddle", followed later by more elaborate padded designs. The solid saddle tree was a later invention, and though early stirrup designs predated the invention of the solid tree, the paired stirrup, which attached to the tree, was the last element of the saddle to reach the basic form that is still used today. Today, modern saddles come in a wide variety of styles, each designed for a specific equestrianism discipline, and require careful fit to both the rider and the horse. Proper saddle care can extend the useful life of a saddle, often for decades. The saddle was a crucial step in the increased use of domesticated animals, during the Classical Era.