Like many ancient fox hunters, I have a pair of equally ancient Dehners. When kiddos were young, we were forever on the tall boot hunt as kids grew --finally, when youngest DD hit the big leagues and stopped growing, we decided to buy her a really good pair of new boots. We talked with a few reps. What sifted down to us was that boots are no longer made the way my 40+ year old Dehners were made. Steers, from whom hides are made into leather, are harvested at a much, much younger age. There is very little “old steer hide” to be had. Older steers had thicker hides. Modern boots are made with hides that are younger and thinner. Therefore, boots don’t last as long.
Along with that is the fashion culture --my 40 year old boots are no zipper stove top hunt boots. While correct for the hunt field, it is unlikely they would be welcomed in the Dressage ring by a teenage rider --heavy and stiff would describe them. I put them on with boot hooks and take them off with a boot tree.
My suggestion would be to never ride/school/walk in your expensive boots except at shows --my own DD does not follow this --she will walk courses in her boots, wear them for lessons, etc. She now buys her own boots and replaces about every 5 years.
Meanwhile, I only wear my ancient Dehners for The Blessing of the Hounds, Joint Meet, [all the members of my hunt switch to winter riding boots like Ice Riders after those two very formal (shadbelly) hunts] and the once-a–year Dressage show I attend (missed this year as Hugh Jackman is lame).