In recent times, an intriguing surge in interest has been noticed for sidesaddle riding. Let’s assume that you, as the rider, have already honed your cross-saddle riding skills adequately to steer your horse smoothly. Regardless, it’s crucial that your riding instructor chooses a calm and sensible horse for your lessons. This will ensure a safer, more comfortable learning environment.
The Art of Mounting the Saddle
The first step, as expected, lies in mastering how to mount. Among the various methods, getting a ‘leg up’ should be your go-to for seamless mounting. This technique doesn’t involve the old-school way of stepping onto your horsekeeper’s hand or relying on a gentleman who doesn’t mind getting his hands dirty to help you. Rather, this approach recommends a niftier method, involving a push at the ankle.

Forceful Ankle Push: A Preferred Method
The push required for sidesaddle is somewhat stronger in comparison to cross-saddle mounting. This extra momentum propels the rider to land on the saddle such that both legs end up on the near side of the horse. Once in this position, the rider can smoothly swing into the pommels. This smart, friendly technique aims to streamline the mounting process, making you feel more at ease and secure on your riding journey.
Three Distinct Methods of Sidesaddle Mounting
In order to successfully master sidesaddle riding, it’s important to become familiar with three distinct methods for mounting the saddle. Each method serves its own purpose and can be useful, depending on your specific situation and level of expertise.
The Cross-Saddle Approach
The first technique is the most common method, involving a cross-saddle approach. Begin by positioning yourself with one leg on each side of the horse. From here, you can effortlessly swing your right leg over the saddle and secure it around the top pommel.
Mastering the Assisted Leg Up
The second method requires assistance from an experienced helper, as there’s a certain level of finesse involved. Your helper must be skilled in lifting you up while also ensuring that your skirt remains out of the way. Once your right leg is positioned on top of the pommel, your left leg can smoothly slide into position under the lower pommel.
Mounting with Confidence and Control
The final technique empowers you to mount your horse without any assistance. To achieve this, stand facing the horse’s head and hold the reins in your left hand. Place your left foot into the stirrup without putting your entire weight on it, as doing so allows the knee to bend away from the horse. This provides adequate space for your right leg to pass between the knee and the saddle. Once again, be cautious and keep your skirt well tucked away on your left side, ensuring a seamless mounting experience.
The Initial Stages of Sidesaddle Riding

Attaining mastery in sidesaddle riding entails understanding and applying a few key techniques. Initially, these steps might feel a bit challenging, but with time and practice, you will soon get the hang of it.
Understanding the Cross-Saddle Position
When you first sit on a sidesaddle, your legs should be in a cross-saddle position. It’s vital that you position yourself in the center of the saddle. Ensure that your right hand is resting on the balance strap while keeping your shoulders square and your eyes looking straight ahead through your horse’s ears.
Swinging Your Right Leg Over
Next, you’ll need to swing your right leg over and around the top pommel – remember to keep your body straight while doing so. You might notice a slight twisting sensation above your hips – don’t worry, this is pretty normal. Make sure the center seam of your breeches aligns vertically with the saddle’s channel. Afterward, take the reins in your left hand while keeping your right fingers touching the balance strap. Maintain leveled shoulders to help you settle comfortably in the saddle.
The Comfortable Paces: Walk and Canter
Typically, as a new sidesaddle rider, the most comfortable paces you’ll find are the walk and the canter. After some practice, your instructor should verify and help correct the position of your legs.
The Importance of Leg Positioning
For better stability, point your right toe downwards and your left toe upwards. Such a position pulls your right knee into the top pommel, providing a firm seat. Meanwhile, the pointing of the right toe ensures your skirt hangs nicely while riding. Your left knee should rest comfortably against the saddle with enough space to pass your hand between your left thigh and the under pommel.
The Role of the Stirrup in Sidesaddle Riding
Initially, avoid using a stirrup for the first two or three lessons to prevent yourself from relying heavily on it. Too much weight on the stirrup can cause you to unbalance your saddle and risk falling off. When you do start using a stirrup, treat it mainly as a foot rest and not as a primary support structure. Remember, persistence and consistent practice will ensure a rewarding sidesaddle riding experience.
Selecting a Comfortable Horse for Sidesaddle Riding
Choosing a horse that’s well-suited for sidesaddle riding can make all the difference, ensuring a smoother, more enjoyable riding experience.
The Importance of a Controlled Trot
Certain horses tend to be more comfortable with sidesaddle riders than others, and a slow, controlled trot is key to gauging this comfort level. This particular pace, distinct from a collected trot, is more common among horses with advanced dressage training. A controlled trot is a comfortable pace for both cross and sidesaddle riders when attempting a sitting trot.
Avoid Rising in the Early Stages
For beginners in sidesaddle riding, it’s advised not to attempt rising during the initial stages of training. In the past, many side-saddle horses were uniquely trained to accommodate the needs and preferences of female riders.
The Significance of a Comfortable Slow Canter
Historically, a lady’s sidesaddle horse was expected to be light in hand and capable of performing a leisurely slow canter, focusing primarily on the off fore. It was believed that cantering on the near fore would jolt the rider into her pommels, diminishing the experience’s comfort. The slow canter allowed ladies to ride gracefully while their escorts trotted alongside them, improving the overall experience.
The Evolution of Sidesaddle Riding Preferences
Previously, the treasured lady’s hack was sought after for its ability to prioritize the off fore during a canter. However, today’s standards have evolved. What was once considered a skilled, well-schooled horse is now deemed one-sided, inadequately trained, and ultimately discarded. Contemporary sidesaddle riders prefer a more balanced and versatile equestrian companion.
The Role of Supervision in Learning Sidesaddle Riding
Embarking on the journey to learn sidesaddle riding, like any other skill, requires a healthy dose of guidance and supervision. Here are a few crucial elements to consider.
Importance of Continuous Supervision
Initially, substantial supervision is needed while learning sidesaddle riding. This isn’t merely a suggestion but a critical aspect of learning. Having an experienced eye on your technique can help ensure you maintain the right posture and correct any mistakes in real-time.
Perfecting the Sidesaddle Posture
While riding sidesaddle, it’s crucial to sit straight. This means keeping your shoulders level and not allowing your left hip to collapse. As a sidesaddle rider, an elegant, upright posture is essential for a fluid ride.
Maintaining Elegance and Confidence
A forward head posture is a common mistake made by beginners, which can disrupt the overall elegance of the rider. Imagine the sight of a rider wearing a top hat, hunched forward: it’s less than ideal. Hence, always remember to hold your head high with grace, as it contributes a significant part to the overall aesthetic appeal of being a sidesaddle rider.
The Evolution of Attire in Sidesaddle Riding
The attire worn during sidesaddle riding has undeniably undergone significant transformations over the years. Let’s delve into the changes and specific nuances related to sidesaddle riding outfits.
The Rarity of Sidesaddle Breeches
Historically, special sidesaddle breeches were tailored for ladies, but today, such specialized tailors have become few and far between. These breeches were designed to fit snugly and smoothly under the right knee when bent around the pommel.
Adapting to Changes with Cross-Saddle Breeches
In recent times, due to the scarcity of custom-made sidesaddle breeches, most riders wear their cross-saddle breeches under their dark skirts. The sight of these light-colored breeches has even become somewhat of a trend. This is quite a departure from the old days when ladies’ breeches were custom-made from the same fabric as their riding habits.
Solving the Rubbed Knee Issue
If wrinkles in your cross-saddle breeches are causing a rubbed right knee, a practical solution would be to place a small piece of sponge under your knee. This simple trick can help smooth out the wrinkles.
The Evolution of Sidesaddle Fashion
Just like in any other domain, fashions in sidesaddle riding have noticeably changed over the decades. For instance, in the early 1920s, it was considered more fashionable for a lady to keep her left foot concealed. However, today it’s quite the opposite, with more of the left boot being visible considered chic. However, this long leg effect could potentially cause the rider to slide off the saddle unless she applies a firm grip with her left knee.
Choosing Practicality Over Fashion for Longer Rides
For practicality during hunting and long rides, I’d suggest opting for a shorter stirrup and leg position, which helps the rider stay securely on top of the saddle. A common fashion faux pas among the younger generation is riding sidesaddle with the right toe sticking out from under their skirts. This significantly disrupts the flow of the skirt and is, in my opinion, a tailor’s nightmare!
The Art of Perfecting the Sidesaddle Riding Posture
Understanding the right position to maintain while riding sidesaddle can be tricky, but with a little guidance, it can become second nature. Let’s take a more in-depth look at this.
The Importance of the Right Seat Bone and Thigh
A crucial aspect of sidesaddle riding is that all the weight is borne by the right seat bone and thigh. Pressing the right thigh onto the right side of the sidesaddle is instrumental in achieving the correct posture. As a rule of thumb, you should be able to slide a hand underneath the left seat bone of a properly balanced sidesaddle rider.
The Unusual Twisting Posture
The sidesaddle posture could seem a bit unnatural initially, as the rider’s body is slightly twisted to the right. However, with the support of the pommels, riders can feel surprisingly secure in their saddles. In fact, many find that dealing with bucking horses is easier when riding sidesaddle compared to astride.
The Advantage of a Steadier Hand
One of the main advantages of riding sidesaddle is the ability for small, light riders to maintain a steadier hand. The conventional wisdom that says a lady’s hands are more precise might stem from this very reason. Because a sidesaddle provides a firmer, more independent seat, the rider’s hands become steadier, leading to significantly better control.
Asserting Control over Larger Horses
Another aspect in which sidesaddle riding shines is that it allows smaller riders to control larger, heavier horses with ease. Not only is this a practical advantage, but it also presents an aesthetic charm when a petite rider takes charge of a heavyweight horse. For instance, both my daughter and I have experienced the thrill and joy of showcasing huge horses in the show ring while riding sidesaddle.
Mastering the Jumping Technique in Sidesaddle Riding
Learning to jump while riding sidesaddle may take a bit of practice, but with the right technique, you’ll soon find it quite an enjoyable and smooth undertaking.
Adopting a Forward Position
To execute a successful jump in sidesaddle riding, a lady must adopt a forward position similar to that used in cross-saddle jumping. This proper positioning will make the entire process of jumping not only effortless but also comfortable. As you get accustomed to this position, you’ll find that jumping in sidesaddle can be both exhilarating and seamless.
Frequently Asked Questions About Sidesaddle Riding
Q: Is sidesaddle riding safe?
A: Absolutely! While it may look a bit unconventional compared to cross-saddle riding, sidesaddle riding is very safe once you learn the correct techniques. Just like any other type of horse riding, one must wear appropriate protective gear and follow standard safety guidelines.
Q: How long does it take to learn sidesaddle riding?
A: The learning time frame can vary for each individual. If you’re already experienced in horse riding and have a good sense of balance, you could get the hang of it faster. On average, you might need a few weeks of regular practice to become confident with sidesaddle riding.
Q: Do I need a special kind of horse for sidesaddle riding?
A: No, any horse can be ridden sidesaddle. However, it’s important for the horse to be well-trained and comfortable with a sidesaddle rider. As with all types of riding, communication, and trust between the horse and rider are key.
Q: Do I need a special saddle for sidesaddle riding?
A: Yes, you’ll need a specially designed sidesaddle. Sidesaddles have a unique design that enables the rider to sit sideway. They typically feature two pommels, which provide stability and support to the rider.
Q: Can things like jumping and dressage be done with sidesaddle riding?
A: Certainly! Once you’ve mastered the basics of sidesaddle riding, you can absolutely do activities like jumping and dressage. It’s actually quite a sight to behold when done correctly!
Q: How is the stirrup adjusted in sidesaddle riding?
A: In sidesaddle riding, the stirrup is typically adjusted a bit longer than in astride riding. In fact, while seated comfortably, your foot should rest easily in the stirrup without having to stretch.
Q: Can men do sidesaddle riding?
A: Historically, sidesaddle riding was designed for women due to the restrictive clothing of the times. However, there’s no actual rule that prevents men from riding sidesaddle. In fact, some men do enjoy it!
Q: Are there competition levels for sidesaddle riding?
A: Yes, there are competition levels, and riders can advance similarly to traditional riding styles. They can start at beginner levels and progress to more advanced levels as they gain experience and expertise.
Q: Is sidesaddle riding comfortable for long rides?
A: Once you’re accustomed to the posture and technique, sidesaddle riding can be quite comfortable for long rides. However, as with any style, it can become uncomfortable if the saddle doesn’t fit your horse properly or if you’re in an incorrect position.
Q: Can children do sidesaddle riding?
A: Certainly! Children can learn sidesaddle riding, but it’s recommended they have a solid foundation in traditional riding first. As always, proper safety gear and adult supervision are essential when children are involved in any equestrian activities.