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I'd say skip over half-chaps and go straight to tall boots. A good pair of tall boots (such as Ariats) will last you years, and you won't have to worry about upgrading from half-chaps to tall boots if you decide to compete, if at all. I love my tall boots, and no matter if I'm riding English or Western, or just doing ground work or barn chores, I'm in my tall boots.

If you call Dover Saddlery (who carry Ariat boots and have wonderful customer support), they will walk you step by step through the measuring process to get the correct sized boots. I'm sure you could also call Ariat directly, I just preferred called Dover because they are known for being English-oriented, not 'all-around' sales-oriented for English, western, and work boots.

I bought my boyfriend paddock boots for his birthday, and I'm kicking myself in the butt for not spending a tad bit more and just getting him tall boots since I'm fairly certain he will continue riding and one day will need to upgrade to tall boots.

One thing to be wary of is how people think tall boots are supposed to fit - when I bought my first pair, I was told to fit them so that the tops of the boots rest right under my knee cap and up in the joint of my knee because they will shrink a couple of inches - I call bogus. I hated that first pair of tall boots, because they never felt good to wear, even after breaking in. The woman I talked to at Dover Saddlery set me on the straight path, and now my tall boots are my most comfortable pair of footwear.

Also, a good trick to breaking in new tall boots is to get them wet and then wear them until dry - it's a quick and dirty way to mold them to your legs and feet. Someone I competed with would stand in a water trough, soak them through, and ride as many horses as she could until they dried. She would compare them to custom-fit boots by the end of this process. It works, just make sure you care for the boots after the process, should they need any cleaning and conditioning.
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