I LOVE tall boots. Its all I ever ride in. I find them so much more stabilizing and comfortable. I really don't like paddocks for riding. I just don't feel comfortable. But almost everyone else at my barn rides in them. I like the look and the feel of talls, and I feel better riding in them.
I do admit they are a pain in the heat, but I will usually just ride indoors if it is to hot out. I don't think I'm ever going to be able to ride in anything but talls.
I wore down a pair, had them for 6 years until the zip broke, and had to wait two weeks for my new pair to ship. I had to ride Wanglish, aka western boots with english saddle. (term can be applied to swapping gear, like western saddle and english bridle). I couldn't hardly stand it. Those weren't the best rides, something just felt really off.
So put my vote down for talls!
~He knows when you're happy
~He knows when you're comfortable
~And he always knows when you have carrots.