[Avna]

I'm the counter-argument -- I can't think of a reason to ride in tall boots. I mainly trail ride and my half chaps plus Ariat Terrains work 100% of the time for everything. No chafing. If I need to get off and clamber up rocks, I'm all set for it. If it's too hot, I ride with thin tights and and use sheepskin tubes on my leathers. If it's super cold, same thing, only thermal tights and insulated snow boots under a riding skirt. Four season versatility.

Only reason I can think of to get those one-purpose boots that cost a mint (mine would have to be custom as I am very short-legged) is to wear the regulation dress-up at a show, a show I will never enter as I've no interest. Terrains and half chaps are just fine for lessons too.

 

[Avna]

I think it's different strokes for different folks. I never show, but I'm happier riding in my tall leather dress boots than I am in anything else. They fit really well, they're less bulky than having short boots and half chaps, and I love having leather against the flap because I can customize how much grip it gives me based on what products I use on it. Plus it's less fiddly than putting on boots + chaps. I just stick my foot in, zip one zipper, and I'm ready. Instead of unlacing my paddock boot, sticking it on, lacing it up, maneuvering the half chap into position, zipping that... I mean, I DO like that my boots look good, I won't lie, but that's not my main reason for enjoying them.

Imagine how you'd feel bushwhacking through an overgrown trail and having them get scratched and scraped. Or trying to lead your horse down a washed-out ravine and sliding in the gravel. Getting soaked in a summer rainstorm. Riding in heat and humidity. Riding in single digit temps -- impossible to keep your feet warm.

Maybe that's not the kind of riding you'll ever do, and maybe nothing like what the OP has in mind either. Those are issues for me though. I mean, I'd like to look spiffy myself ... but would rather be practical.