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Step 1
Decide what type of sidesaddle riding you want to do. Just like astride saddles, you can find jumping, flat and western sidesaddles. If you like costuming and re-enacting, you might consider a period sidesaddle instead of a modern one.
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Step 2
Decide whether you want a new sidesaddle or a used sidesaddle. Older sidesaddles often do not fit modern horses - they're made for narrow horses with high whithers. If your horse has a wide back, you may need to look at a new sidesaddle.
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Step 3
Decide on a price range. Older, well-made sidesaddles such as Martin and Martin, Owen and Champion and Wilton are quality saddles, but they cost much more than some of the new sidesaddles.
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Step 4
Learn about good sidesaddles. Unfortunately there are many poor quality sidesaddles out there. They're difficult to ride in and uncomfortable for both you and the horse. Books such as Sidesaddle Legacy and organizations like the American Sidesaddle Association can help educate you about quality sidesaddles.
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Step 5
If you decide to look at a new sidesaddle, contact one of the sidesaddle dealers like Hundred Oaks, Inc. Since sidesaddles are still specialty items, only a few companies offer new sidesaddles. Avoid those sidesaddles built on an astride tree and those of poor quality construction. They will be difficult, if not impossible, to ride in and will break down.
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Step 6
If you decide to search for an older or used sidesaddle, begin your search at local tack shops. Let the owners know you are searching for a sidesaddle and ask them to let you know if they receive one.
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Step 7
Check out garage sales, estate sales and auctions. Sidesaddle enthusiasts occasionally find quality saddles at bargain basement prices at garage sales, estate sales and auctions.
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Step 8
Join a sidesaddle organization and watch for classified ads on their website, in their newsletter and on their email list.
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Step 9
Once you find a sidesaddle, examine it carefully to make sure the tree is in good shape, the leather is not brittle or frayed and that the stitching is not loose.
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Step 10
Have an experienced saddler check your saddle fit. If no one is available in your area, an experienced sidesaddle repairer may be able to assist you through photographs.
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Step 11
Enjoy your sidesaddle!
