Sidesaddle: History, Facts, & More On This Old Riding Style

Seeing the topic of sidesaddles coming up frequently and watching several sidesaddle classes during my time working at the Scottsdale Arabian Horse Show pushed me to create this article. Researching this style of riding has taught me so much about the history of riding in general as well as how the sidesaddle style came about. I was amazed by all the ways that sidesaddle was ridden. Not only is there an English style, but there is a western style for side saddle too! And did you know that there are sidesaddle jumping competitions as well? This unique riding style has definitely caught my attention and after learning so much about it I want to share this information with you.

Sidesaddle is one of the oldest styles of riding that ladies could partake in. The rider sits in a unique saddle designed to carry the rider sideways. Sidesaddle is not seen very often anymore except for in horse shows or certain displays. Way back then, when the sidesaddle riding style was popular, women were not allowed to ride with their legs around the horse. If a woman wanted to ride they needed to sit sideways as it was seen as more ladylike and proper.

What Is Sidesaddle?

Sidesaddle is a riding discipline that is found in both English and Western riding but is mainly seen in English riding. It is a style of riding done by women and girls primarily in the show ring. In this discipline, riders sit slightly sideways on their horse with both of their legs on the left side of the horse. There is one stirrup on the saddle where the left foot rests. There is a leg rest known as the top pommel or fixed head that the right leg goes around. Though riders are sitting sideways, they should still position their body forward and upright.

The History Of Sidesaddle Riding

Did you know that sidesaddle riding can be traced back all the way to before the 1300s? Anne of Bohemia is credited with creating the first functional sidesaddle which was created in the late 1300s (1366-1394). This early sidesaddle was comparable to a chair and had a footrest on the left side of the horse where the rider could put her feet. She rode sidesaddle on her way to marry King Richard II. With time, the footrest was replaced with a stirrup known as a slipper stirrup. The left foot was put in this stirrup while the right leg was bent up and swung freely.

The reason this style of riding was created and used by women was because it was thought to be indecent for a woman to ride astride a horse. It was believed that riding aside rather than astride was a way to protect a woman’s virginity.

Even before Anne created this version of the side saddle, women still rode in this style. The first sidesaddles were actually just pillows attached to a man’s saddle making the rider have to sit sideways in the saddle. A man or boy would then have to lead the horse as the woman was not allowed to steer or ride the horse on her own. This makeshift sidesaddle was known as the pillion.

Later, a saddle with a backrest and footrest was created. This was known as the planchette. This, just like the pillion, had the woman sitting sideways on the horse.

It is unknown by who, but a horn soon was added in certain saddles to support the woman’s right leg while the left leg was in the stirrup. Catherine de Medici is believed to have added the second horn to the sidesaddle to offer even more support to the legs and aid in keeping the left leg in place. By this time, the backrest had disappeared, and instead, a cantle-like piece ran along the whole right side of the saddle. This helped to keep the rider in the saddle and not let them fall over the right side.

For the next few centuries, this was the accepted style of riding for women and as this style developed, women began to jump horses and race them while riding sideways.

This style of riding mainly was developed and created in Europe.

What Is Expected Of The Horse?

Because of the position of the rider in this style, horses ridden in this fashion must be very responsive to their reins. The rider only has one leg free to guide and direct the horse so without a responsive horse, it would be extremely difficult to ride them sidesaddle. These horses also must be strong and able to carry the awkward weight smoothly.

Being extra responsive to the rider’s reins is crucial. A horse must know to stay on the rail when being ridden in an arena and rely entirely on the reins. Otherwise, if the horse is not responsive enough, the rider will not be able to accurately direct the horse in the place they want it to go.

Is Sidesaddle Dangerous?

Sidesaddle can be more dangerous than other styles of riding just because of the position of the rider. Because the rider is sitting at an angle with both legs on one side of the horse, they are not able to grip the horse at all making it much easier to fall off. It is also much harder to ride certain gaits, like the trot for instance and posting is not really doable in the sidesaddle.

If a horse bucks, bolts, or spooks when being ridden sidesaddle over another saddle, the rider is much more likely to fall and be injured in the sidesaddle because of the lack of gripping ability and point of balance.

Parts Of The Sidesaddle

Just like the normal saddle, there are many parts of the sidesaddle that are crucial to know. The parts of the sidesaddle include:

Fixed Head Or Top Pommel

The fixed head, also known as the top pommel is the first horn protruding from the sidesaddle. This horn is where the right leg goes over the horse and onto the left side. The point of the fixed head is to help hold the right leg up and in position.

Leaping Head Or Lower Pommel

The leaping head, also known as the lower pommel is designed to keep the knee of the rider in place. This is similar to the knee roll of a normal English saddle as it too aids in keeping the rider’s leg in position.


This term is an easy one to master. The seat is where the rider sits on the saddle.


The cantle is the very back part of the saddle that usually rises up behind the seat. On a sidesaddle, the cantle is actually relatively flat unless it is a western sidesaddle.


The stirrup is the same as in a normal English saddle or Western saddle only there is only one of them for just the left foot as opposed to the usual two for the left and right feet.


On the stirrup leather there is something known as a keeper. A keeper is used to hold the loose ends of leathers after something has been buckled on a saddle, bridle, or martingale. In this case, it helps hold the remaining leather not used after the stirrup leather has been buckled.

Leaping Head Adjustment Hole

Not everyone is going to be the same size or have the same sized legs so adjusting the leaping head (lower pommel) is important to give the rider the support they need no matter their leg size.


The skirt on a sidesaddle is small and is just big enough to hide the stirrup bar. The skirt can be found at the top of the stirrup leather covering the top of the leather.

Stirrup Bar

The stirrup bar is a piece of metal rigging under the skirt where the stirrup leathers attach to.


The flap is exactly what it sounds to be. It is basically the flap on the left side of the saddle that covers the girth attachments and keeps them from touching the rider’s legs.

Stirrup Leather

The stirrup leather is the thick leather strap that the stirrup attaches to. In western sidesaddles, this would be considered the fender. This attaches to the stirrup bar up under the skirt.

Over-Girth Billet

This billet is buckled under the horse’s belly to make the horse’s saddle more stable. This is a safety measure that keeps the saddle in place in case anything were to go wrong. This attaches under the horses belly.

Off Flap

The off flap is basically the smaller flap on the right side of the sidesaddle. this is known as the off-side as this is not the side the rider’s legs are and it is the side that much of the buckles are. This ‘off side’ is side less paid attention to.


The over-girth is what attaches to the over-girth billet. This fastens under the horse’s belly and is a safety device used to keep the horse’s saddle in place in case something were to go wrong or break.

Balance Billet

The balance billet is a billet strap attached to the back of the saddle that attaches to a balance girth. This helps to keep the saddle upright and pull it to the right while the rider’s weight pulls it to the left, therefore balancing it.

Balance Girth

The balance girth helps to balance the saddle and pull it to the right to balance the weight out from the rider. The girth pulls to the right and the rider pulls to the left.

Fitzwilliam Girth

Some sidesaddles are equipped with a Fitzwilliam girth which is a cushioned comfortable girth.

How Long Does It Take To Train A Sidesaddle Horse?

To answer this question is actually kind of hard. It all depends on the sensitivity of the horse and how well they respond to your hands. The key is having a horse that responds well to your hands.

Because sidesaddle trainers are hard to come across, it may take even more time to find a trainer than it is to actually train the horse. It can take around two years of frequent training to get your horse used to the awkward weight and the responsiveness to your hands.

What Tack Is Used When Riding Sidesaddle?


The most important piece of equipment used in this discipline is the sidesaddle. This is the key to the sport. Without this piece of tack, you can’t ride sidesaddle.


Sometimes a double bridle is used (a bridle with two bits) to better guide and control the horse’s head. Other times an average bridle you would see in any other discipline is used. It all depends on the horse and its needs.

What Styles Of Sidesaddle Riding Are There & What Can You Do When Riding Sidesaddle?


Most of the sidesaddles you will see out there are English sidesaddles. They have an overall look of an English saddle but with the two horns or pommels.


Western sidesaddles have the typical western look to them when you are looking at the saddle’s decoration, leather tooling and other features. They are the same heavy large saddles you will see in other western disciplines but instead of having a saddle horn, the saddle has the two pommels.


Sidesaddle jumping has been around since the early 1900s and late 1800s. It consists of the same jumps you might see in showjumping only the rider is sitting sideways o their sahorse.


Sidesaddle racing is a popular sport among sidesaddle riders though it isn’t a high-level sport. There aren’t any professional sidesaddle races that go high up to derby level competition, but still, the competition is hot. This is a unique event as all the riders are sitting sideways on their horses. Because they are riding sidesaddle, it is a dangerous event as it is harder to stay on the horse in this position.

What Do Sidesaddle Riders Wear?


Just like in any other riding discipline, Sidesaddle riders wear boots. The boots should have a good heel as to ensure the rider’s foot does not slide through their stirrup.


Riders in side saddle wear a skirt especially designed for sidesaddle riding. One side of the skirt is cut out to allow the rider to put their legs where they want them on the saddle, the other part is long and sometimes decorated and that is the side that shows outward to their audience. The skirt is usually the same color as the rider’s jacket and hat but it doesn’t have to be.

Collared Shirt

Under the show jacket, a rider will wear a collared shirt, usually white in color. This shirt completes the look.

Show Jacket

Just like in show jumping or hunt seat, side saddle riders wear a show jacket. This usually matches the color of their skirt but it doesn’t always have to.


Sometimes a tie is worn under the show jacket but not always; the tie can be nearly any color.

Top Hat

A top hat or something similar is often paired with the rider’s apparel and is often the same color as the jacket and skirt. Sometimes a flower or feathers will adorn the hat. A decorated hat is not an uncommon sight.


Some riders prefer to wear gloves when riding to offer them extra grip. In sidesaddle the most common gloves seen are black and white. Not only do they help the rider control their horse, but they also give the rider a more professional and ‘lady-like appearance.’

Hailey Sipila

Horses have been my passion ever since I can remember. At school, I was known as that weird horse girl, and I would read horse encyclopedias for fun. Over the years since those days, I have only learned more. My experiences with horses of a variety of breeds have taught me a lot. Now I want to share what I know with you!

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