Sidesaddle Riding: A Timeless Equestrian Tradition
Sidesaddle riding, often called riding aside, is riding with both legs on the same side of the horse using a saddle built for sideways balance. Done well it looks steady, quiet and precise, and it carries a long tradition that still turns up in show rings and clinics today. Most people come to it after finding an old saddle in a tack room, watching an aside class at a show, or wondering whether it is genuinely safe to try. The honest answer is that it can be very safe and very stable, but only with equipment that fits the horse properly. This guide covers the history, how the saddle works, what to wear now, and the basics of riding and safety.
What sidesaddle riding is
The whole discipline rests on one idea: keeping a rider secure and balanced with both legs to one side. It developed in Europe partly because women's clothing made astride riding awkward, and partly because social customs treated straddling a horse as immodest.1 Modern sidesaddle is not just costume riding. Riders train for balance, straightness and clear aids, then take those skills into showing, dressage, pleasure riding and some jumping, depending on the rider's experience, the horse, and the saddle's fit.
A brief history
Early aside seats appear in ancient and medieval imagery, but many of those show a passenger arrangement, with women perched sideways, sometimes led, with limited control.1 Over time the saddle evolved into a true riding saddle that allowed independent control and, later, more athletic work. By the nineteenth century sidesaddle was widespread in Britain and parts of Europe and North America, particularly among women of the upper and middle classes. It became closely tied to formal riding culture and the fashion of long skirts, which were practical on the ground but hazardous in the saddle unless managed carefully.1
How a sidesaddle works
The saddle does the balancing work that a second leg normally would. A modern English sidesaddle has a seat that positions the rider slightly offset, plus two main supports usually called horns or pommels:
- Fixed head (upper pommel): the rider's right leg hooks around this for stability.
- Leaping head (lower pommel): supports the rider's left thigh and helps prevent the rider sliding forward or left during movement and jumping.
Because the rider's legs are not symmetrically placed, the saddle must be correctly built, correctly flocked, and fitted to the horse with particular care. A sidesaddle that slips, bridges, or pinches can create uneven pressure, sore backs, and a rider who is forced to brace, which is never a good combination.
Equipment and attire
At a minimum you need a correctly fitted sidesaddle, a suitable girthing arrangement (often point and balance straps, depending on saddle design), and a breastplate or balance strap if a knowledgeable fitter recommends one for that horse's shape and workload. If you are new to sidesaddle, borrowing a saddle is common, but only if it genuinely fits the horse and sits level and stable when mounted.
Traditional turnout often uses a long skirt or apron worn over breeches, with a fitted jacket and gloves. Many modern riders keep that silhouette but update the safety layer underneath. The current best practice is simple: wear a properly fitted, fastened riding helmet, even if the rest of the outfit is traditional.2 Many riders also choose a body protector, particularly when learning, riding young horses, or doing faster work.3 If you do wear a skirt or apron, it must be designed for riding aside so it sits cleanly, does not bunch under the seat, and cannot flap into the horse's flank or snag on the saddle. Loose everyday fashion skirts are a bad idea around tack.
Learning to ride aside
The seat looks effortless because the rider is doing quiet, precise work. Most riders mount from a mounting block to reduce strain on the horse and avoid twisting the saddle. The details vary by saddle and rider, but the principle is the same: keep the saddle still, settle softly into the deepest part of the seat, and organise your legs without rushing.
Sidesaddle balance is not about perching. A good aside seat looks quiet because the rider is stacked, ear over shoulder over hip, then subtly rotated to match the saddle's design. The torso stays tall and elastic, with the pelvis allowed to follow the horse's back rather than locking against it. Many riders find they need to rebuild their feel for straightness. Without a leg on each side it is easier to accidentally collapse a hip, twist the shoulders, or grip with the right thigh. A good instructor will keep bringing you back to stillness: soft hands, steady breathing, and weight placed deliberately.
Astride riding gives equal contact on both sides of the horse. Aside riding asks for more precision in balance and timing, because some of your usual symmetry tools are gone. The horse should still travel straight, forward and relaxed; the rider simply uses different geometry to get there. A few practical points help more than they should:
- Start on a steady horse with a comfortable, regular rhythm.
- Prioritise saddle fit before you worry about looking right. A slipping sidesaddle teaches bad habits fast.
- Build core endurance gradually with short rides and frequent breaks. Tension is the enemy of balance.
- Use an experienced sidesaddle coach or mentor. The small adjustments matter more than they do astride.
Safety and welfare
Comfort for the horse is the whole story, and rider safety runs alongside it. For riders, the baseline habits are familiar but worth stating plainly:
- Wear a correctly fitted helmet and fasten it every ride.2
- Consider a body protector when learning, jumping, or riding in higher-risk settings; fit matters as much as the model.3
- Avoid second-hand helmets if you cannot verify their history and condition.2
- Check stability before leaving the yard: girths even, saddle level, no rolling when you put weight in the stirrup.
For the horse, a sidesaddle must sit level, distribute pressure appropriately, and allow free shoulder movement. If the horse begins to shorten the stride, hollow the back, swish the tail, or resist being mounted, pause and reassess fit and soreness before you assume it is attitude. Groups such as Side Saddle Australia exist because the discipline needs shared standards, particularly around tack fit, judging, and safe participation.4
Sidesaddle in Australia today
Sidesaddle has never fully disappeared, but it has become more visible again through historical sport, show rings, clinics and dedicated aside classes. In Australia, Side Saddle Australia was formed to promote the discipline nationally, support rider education, and encourage consistent standards for competition and events.4 If you are curious, the simplest entry point is a supervised try-out on a suitable horse, in a saddle that is known to fit. The feeling is distinctive: not fragile and not theatrical, just a different way of staying with the horse's movement.
The bottom line
Sidesaddle riding endures because it is functional as well as beautiful. The best rides aside look almost uneventful: a horse moving freely, a rider sitting quietly, and a saddle that does its job without drama. Get the fit right, keep the safety basics modern, and learn from people who do it often. The rest follows in small, steady steps.
References
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