(Photo: John Harwood)
The story goes that in 1382, Princess Anne of Bohemia rode across Europe to meet and marry King Richard II of England. She rode on a special saddle designed to protect her hymen from being ruptured, which might take place if she rode for an extended period of time astride her horse.
This saddle was the side saddle: a chair-like saddle that permits a woman to ride a horse while wearing a long skirt. Some noblewomen developed the concept into a refined and fairly practical design. Ella Morton writes at Atlas Obscura:
In the 16th century, Catherine de' Medici pioneered a more practical, manageable side saddle design. It used a stirrup rather than a footrest, placed the rider facing forward, and secured the right leg with a pommel. This design allowed the rider to control her own horse, and made her less likely to fall off—but was still less stable than riding astride.
Further innovations, such as a second pommel at the top of the left thigh, gave riders additional stability. The practice of riding side saddle peaked during the 1930s. Thereafter, women riders tended to prefer to just wear pants and sit astride their horses on conventional saddles.
Yet, surprisingly, side saddle riding is making a comeback. In the US, the International Side Saddle Organization (ISSO) is among its proponents. It helps guide standards and practices for equestrian competition while riding side saddle:
Side saddle today comes in many guises. Some riders compete in equestrian events that have strict rules regarding dress, behavior, and appearance. If you want to enter a Hunter Class event in the U.S., for instance, the United States Equestrian Federation requires you to adhere to a lengthy list of guidelines. Your gold tie pin must sit horizontally rather than vertically, your coat buttons must be "black bone," and, in accordance with traditional hunting equipment, you need to carry a sandwich case and flask on your person. Not only that, the sandwich case "must contain a sandwich, wrapped, and flask must contain sherry or tea.”