A gnawing question to be sure. Unless of course you live in the 19th century (or are a nice normal person with no interest in antiquated styles of horse riding whatsoever). We can't help you in the latter case, but for the former the answer is fairly simple. With the exception of unusual circumstances and emergencies (remember Melanie Wilkes galloping away astride when the Yankees came to Tara?), Victorian ladies rode aside on their horses, with the aid of a sidesaddle. Were there women who chose to ride astride? Sure, but the majority continued to use the sidesaddle until the feminist movements at the onset of the 20th century started to vocally oppose the practice.
In some ways, we could say sidesaddles shared the fate of hoop skirts. They would both be ridiculed and demonized by later movements as instruments that kept women in a perpetual state of helplessness, but, at the time they were introduced, they actually represented a step forward to women gaining autonomy. Just like the metallic hoop skirts greatly diminished the weight of the undergarments a woman was supposed to wear and made walking easier, the 19th century sidesaddle made riding and even jumping safe(r) for women.
You see, the first medieval sidesaddles were simply modified seats fastened on a horse, with the passenger facing sideways and having little or no control over the animal's movements. The horses were usually led by someone else. This system solved the issue of modesty quite well, but it offered no middle ground. A woman wanting to ride would have to do it astride, a woman wanting to be ladylike would have to move at a snail's pace or be led.
The modern sidesaddle probably evolved from a regular cross-saddle, on which two pommels were strategically placed to hold into position the rider's right leg while allowing her to face forward. We can actually get a pretty good idea on how the modern position was born from Gone with the Wind itself. Here's Scarlett, having only a man's saddle at her disposal but still wanting to ride in the proper way--with her legs not showing from under her skirts:
In some ways, we could say sidesaddles shared the fate of hoop skirts. They would both be ridiculed and demonized by later movements as instruments that kept women in a perpetual state of helplessness, but, at the time they were introduced, they actually represented a step forward to women gaining autonomy. Just like the metallic hoop skirts greatly diminished the weight of the undergarments a woman was supposed to wear and made walking easier, the 19th century sidesaddle made riding and even jumping safe(r) for women.You see, the first medieval sidesaddles were simply modified seats fastened on a horse, with the passenger facing sideways and having little or no control over the animal's movements. The horses were usually led by someone else. This system solved the issue of modesty quite well, but it offered no middle ground. A woman wanting to ride would have to do it astride, a woman wanting to be ladylike would have to move at a snail's pace or be led.
The modern sidesaddle probably evolved from a regular cross-saddle, on which two pommels were strategically placed to hold into position the rider's right leg while allowing her to face forward. We can actually get a pretty good idea on how the modern position was born from Gone with the Wind itself. Here's Scarlett, having only a man's saddle at her disposal but still wanting to ride in the proper way--with her legs not showing from under her skirts:
