So you want to ride side saddle?
There are few things you need to think about first:
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Do you have your own horse or pony, or do you lease, borrow or share a ride on someone else's horse or pony? If you are NOT the owner, you should check that the owner is happy about your plans first.
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Next, think about whether your mount is suitable for side saddle. Looks and breeding aren't everything - the main consideration is that the horse or pony is "a safe and comfortable ride for a lady".
That means
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Well-mannered and obedient
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Calm, willing temperament
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Suitable conformation - good length of back to carry a side saddle and a good shoulder and wither to help keep it stable
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Free-moving, with smooth, even paces and straight action - and it helps if the trot is not too bouncy!
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A good mouth and good brakes!
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No buck, nap and DEFINITELY no rear!
For safety reasons, you should NEVER attempt side saddle on a known rearer.
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Most horses and ponies take to side saddle very quickly easily, and even seem to enjoy showing off.
Next, you need a side saddle...
...well, of course - you can't ride side saddle properly without an actual side saddle...
This is the hard part: to ride side saddle properly - that is, safely and comfortably - you need a side saddle that fits your horse, AND fits you, too - and while you might be lucky, finding a good side saddle is not always either quick or easy, so GET HELP!
Your best course at this point is to contact the NZSSA. Our Area Liaison Officers will often be able to put you in contact with a local member who can help you try out side saddle riding for yourself. Often these people may know of a saddle that can be loaned or leased for a few months to get you started, and may be able to help you out with some basic tips about riding or even arrange some coaching or lessons.
Once you are sure that side saddle is the way for you (and your horse!), you can start looking for that elusive perfect side saddle of your own.