Elisabeth of Austria clearing a fence side saddle like it ain’t no thang. (Image: Public Domain)

At the Pennsylvania Horse World Expo last weekend, Shelly Liggett stood at the front of her booth, waiting for a woman—any woman—to walk by. “I don’t care the age, the size, the shape,” she says. “If they look like they’re a rider, we con them into sitting down and giving it a try.”

“It” is side saddle, the practice of riding a horse with both legs on one side. Liggett is the president of the International Side Saddle Organization (ISSO), a group of horse lovers who like to ride “aside” in addition to astride. At every expo, show, and leisure ride she attends, Liggett is an ambassador for side saddle, aiming to entice dubious riders to take a seat and see how it feels.

Side saddle has been around for centuries, born of a need to preserve female modesty in the age of mandatory long skirts. Its origins have been traced to 1382, when 15-year-old Anne of Bohemia journeyed across Europe on horseback to wed King Richard II. Because of the need to preserve her virtue—or, in plainer terms, “protect the royal hymen”—Anne rode with both legs to one side.

Madame La Comtesse de Saint Geran riding side saddle in the 17th century. (Image: Public Domain)

In the wake of this very proper journey, the side saddle came to be regarded as a handy tool for the preservation of female modesty. Initially it took the form of a chair placed on the horse’s back to face one side. Women required assistance when mounting and dismounting, and would need to be led around rather than controlling the horse themselves.

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.

Sidesaddler Esther Stace clearing 6'6" at the Sydney Royal Easter Show in 1915.

(Photo: Public Domain)

A major side saddle innovation came circa 1830, in the form of the “leaping head,” a second pommel placed at the top of the left thigh. This design change gave women much more stability in the saddle, allowing them to participate in spirited hunts and jump tall fences. Really tall fences. In 1915, side saddle equestrienne Esther Stace cleared a six-foot-six barrier at the Sydney Royal Easter Show.

The one factor still causing havoc, safety-wise, was attire. Long skirts could get caught in stirrups, causing women to be dragged—no article of riding dress has proved such a death-trap as the skirt,” wrote Alice Hayes in her 1903 guide, The HorsewomanThe solution was the side saddle apron, a late 19th-century invention that resembled a long skirt from the front, but had a gap in the back so the legs could be free.

A side saddle apron. (Photo: Public Domain)

In the beginning of the 20th century, an outfit consisting of a jacket, breeches, boots, waistcoat and apron with a silk or bowler hat became standard side saddle riding attire. Side saddle itself peaked in the 1930s, but World War II and its associated shortages and shifting societal expectations of women brought changes. Expensive side saddles were swapped for standard astride models. Modesty was no longer mandatory, and female riders felt more comfortable with one foot on each side of their horses.

This brings us to the present day, and the question: why ride side saddle in the 21st century? It is trickier than the standard way of riding, and seems to endorse fairly outdated associations of femininity. 

Janet Senior, chair of the Side Saddle Association (SSA) in the U.K., says that riding aside “uplifts the rider giving a feeling of grace and elegance.” The SSA was established in 1974, when, the organization says, “riders and spectators began to miss the beauty and elegance which side saddle riders had contributed to the pre-War equestrian scene.” It exists alongside other organizations like the U.S.-based International Side Saddle Organization (ISSO), which was also founded in 1974, to preserve the tradition of side saddle and recruit new riders. 

A side saddle rider at a Concours d’Elegance event in England. (Photo: David Merrett/CC BY 2.0)

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.”

Many side saddle riders, however, ride aside simply for the fun of it. Shelly Liggett of the ISSO says outings involve everything from “historical kinds of things” to “yeehaw shoot-‘em-up cowboy kinds of things.” For historical events, the aim is to recreate looks from the past while making allowances for the conveniences of the present. The ISSO website advises riders that if they need to alter their historical outfit “for safety, budget, or time issues,” they “should be able to explain why, and what the original would have been like.” In other words, swapping out a row of fiddly buttons for a zipper is okay in some cases. 

One issue affecting side saddle ridership is a lack of suitable or affordable equipment. A decent side saddle costs thousands of dollars, and few people make them these days. Most riders use vintage saddles from the 1930s or earlier, but it can be difficult to find models that fit the horse properly and are in good enough condition. In 2014, the SSA addressed this shortage with a campaign called ”Is There a Side Saddle in Your Attic?” As the press release gently asked, “Granny’s side saddle may be a treasured possession or is of sentimental value, but if it is not being used, perhaps you would consider bequeathing, leasing or selling it…?”

A young side saddle rider showing correct form. (Photo: B.Keil 2013/CC BY-SA 4.0)

When a side saddle fits right, you’re in a full riding outfit, and feel balanced and stable, ”you feel connected to a bygone era which links the past to the future,” says the SSA’s Senior. “Every side saddle rider I have ever worked with or met is drawn to that time and place when side saddle riding was in its prime.”

The need for female modesty may be less of a pressing concern for 21st-century riders, but side saddle inevitably brings refinement and poise to the proceedings.