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Do you wear half-chaps now? If not, that would be my next step. Adding them to your paddock boots is cheaper and more practical than buying tall boots, plus it will be easier to find something that fits by using the half chaps-paddock boots combo, rather than tall boots.
 

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I guess I have a really hard time imagining tall boots to be more comfortable than paddock boots + half chaps. Plus my paddock boots just zip. My routine is to put on the paddock boots when I get to the barn, do chores and whatever, and then just put on the half chaps right before I ride, if I ride. I can't imagine doing chores in tall boots. And right now, it's so darn hot that tall boots would just be brutal. I take off the half chaps pretty much the second my ride is over. I take of Pony's bridle, then take off the half chaps, then remove the rest of his tack. That's how hot they are. I couldn't do that in tall boots. Bleah.

Plus, if you think you're going to show but aren't going to do it now, then if you get the tall boots now you have to take really good care of them so they will still look good by the time you get to showing. Why not just get the half chaps now and then get tall boots when you need them? Most lower level shows will accept half chaps+paddock boots as long as they match.
 
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