Have you ever wondered what it would be like to ride side saddle? Is it scary? Is it easy to balance, and is it as comfortable and enjoyable as riding astride?

Whenever I see someone riding side saddle, I’m impressed at how elegant they look. I love the whole picture, the genteel look of the costume and how the skirt drapes across the horse, so I set out to find out more. My first port of call was side saddle guru, Roger Philpot. His passion for the sport means that he has become something of a side saddle celebrity, and he even trained side-saddle stunt woman Pippa Booth, who doubled for Downton Abbey’s Lady Mary.

My first question for Roger is just how hard it will be to adapt to riding side saddle. He explains: “If you’re an experienced rider, you can pick it up relatively quickly on a trained side saddle horse.” Roger also allays my safety concerns, saying: “Side saddles use safety stirrups, and you can hold onto the pommel if you want to. The big difference is that your point of balance is behind your right knee, which is obviously very different to astride riding.”

I admit that the beautiful dresses worn by side saddle riders are part of the sport’s appeal, but Roger tells me that it’s fine to wear your normal astride clothes to learn in, and there are even some classes where it’s not mandatory to wear a habit.”

A little bit of history

Side saddle was the traditional way for a lady to ride – it was impractical to ride astride because ladies wore long skirts. Male grooms even rode side saddle to keep the horses fit for their lady owners. It wasn’t until during the Second World War that the trend for ladies to ride astride developed.

In 1974, Valerie Francis and Janet Macdonald formed The Side Saddle Association to preserve this elegant tradition. In fact, side saddle is not strictly for women and Roger explains that some men are trying it, too. Furthermore, a lot of riders with medical conditions, such as those with back problems and riders who have lost the use of their legs still have the option to ride side saddle, which means that they can continue to ride.

What to wear

In most side saddle classes, it’s customary to wear a habit, which comprises of a jacket and skirt. The skirt is referred to as an apron and is actually a safety skirt, which prevents you being dragged should you fall.

Side saddles have two pommels. The top one is called a fixed head and your right leg wraps around it. The lower pommel is called a leaping head and is moulded in the opposite direction. Roger stresses the importance of a correctly fitting saddle. “The saddle must support the horse and rider, especially under the left seat bone. If it’s correctly fitted and in balance, it allows the rider to concentrate on riding instead of fighting the saddle.”

Because both legs are on the left side of the horse, and your ‘top’ leg (the right) is only used for balancing purposes, a schooling whip or extended cane with a curved end is normally held in the right hand and used on the flank to replace the aids that are normally given by the right leg when riding astride. The aids remain exactly the same as astride riding.

The position

Getting the correct position is vital. Your point of balance is now behind your right knee. Roger explains that I need to use my right leg to grip around the pommel and provide support and balance. My right thigh does most of the work, and my right foot points downwards, which feels unnatural to begin with. My weight is equally distributed through my buttocks, the same as riding astride. The ball of my left foot rests on the stirrup, but with no weight in my heel. Roger guides me through establishing the correct position…

• mount your horse as you would normally, using a mounting block. Sit astride and then place your right leg over the front of the saddle. Your right leg should grip around the pommel with your toe pointing downwards
• place equal weight in your buttocks with your waist facing forward and your upper body turned slightly clockwise at five past twelve
• place the ball of your left foot in the stirrup but with no weight in the heel
• place the loop of your reins over the withers on the off side
• carry your schooling whip in your right hand

With that it was time to begin my first-ever side saddle lesson. Walking was, it turned out, relatively easy, although keeping my right toe pointing downwards felt a bit odd. The warm-up was much the same as I’m used to when riding astride – plenty of transitions and changes of rein. Walking on the right rein felt natural because my body was angled in that direction anyway. Unlike astride, where you face your body in the direction you want your horse to turn, I was facing the opposite way when it came to the left rein, which made it a bit more tricky.

When it came to trotting, I was pleasantly surprised. With my right leg firmly nestled around the fixed head of the saddle, it felt quite comfortable. Roger guided me to establishing a balanced working trot and, thankfully, my mount, Geoffrey, wasn’t too forward-going or reluctant. All the trot work is done sitting – although Roger tells me that Victorian ladies were adept at rising trot.

After a session establishing walk and trot, as well as transitions, I was exhausted – canter would wait for another day. 

Lasting improvement

The next day, when I ride my own horse, I’m amazed at how much more secure and confident I feel. Roger explained that learning another style of riding helps with your co-ordination, and that side saddle helps you to be straighter and encourages you to become aware of your position.

So, I did it. My first side saddle lesson was a success. Was it easy? Well, it wasn’t as hard as I thought it might be, however, there is so much more to learn. Was it comfortable? Yes, in the main. Will I be back for a second lesson? Try and stop me!

Have a go

Expect to pay £30–40 for 30 minutes’ specialist side saddle instruction. Look for an instructor with a licenced horse – this means the horse is trained in side saddle and examined by the side saddle Association (SSA) for its suitability. 

For a list of local instructors and details of ‘have a go’ days where you can try side saddle with your own horse, visit sidesaddleassociation.co.uk