As someone who wore tall boots continually during my teen years into my mid-twenties, I long ago retired them to “special use only” --ie Blessing of the Hounds, Joint Meet, Opening Day. For the past decade I’ve lived in (Ariat All-terrain waterproof) paddock boots. The reason is comfort, versatility, and cost. [ added this: I hunt weekly Sept-April —I only wear leather tall boots for the dates above, the rest of the time hunting, I (and just about everyone else) wear Mountain Horse Winter Riding Boots --or similar --the leather tall boots are saved for the special occasions listed).
I ride first thing in the AM, 2-3 horses. I put on breeches, paddock boots, and half-chaps. Good to go. When horses are done at noon, I switch to chore work --stalls, mowing, spraying, gardening. Tall boots would not work for that. Second reason is I ride both English and Western. When I’m working with horse on Western stuff (I occasionally wear breeches) but usually I wear Western riding pants, no half chaps, but same boots.
Finally, cost. My last (I hope) pair of Dehners Tall boots set me back $900. I can buy Ariats for $100. The Ariat paddock boots generally last about 3-5 years. I have worn out at least 9 pair of tall boots (rough count, can’t recall exactly as my kids and I got to sharing boots at one point). I hose off my Ariats if they are muddy. Those tall boots are kept on trees, polished, in boot bags for when I need them. Don’t want to do that every day.
I initially switched to Ariats when I did a 250 mile trail ride. I was worried that at some point I might need to dismount and lead my horse, possibly up to 20 miles to the next camp (didn’t happen, rode the whole way). Looked for a boot that I could ride in OR hike in. Ariats did just that.
Never went back to daily tall boot use after that.