I've been in the lucky position of owning a pair of leather boots over the last decade that have been super comfortable and didn't require any breaking in. I've literally worn them to death. Soles eventually came off and the shoe repair guy said they are not worth repairing as the midsole is becoming detached as well. Bought a new pair of boots. Same brand, same size, model as close to what I had before and got a blister after a short walk which was disappointing. I'm now left without a pair of boots that I trust not to give me blisters.
An old trout fisherman's trick is to put studs in to wading boots to increase longevity when the sole is falling off. Thought I would apply this to my old boots. I literally pulled them out the bin and fixed the soles in place with screws. It's #8 wire stuff, but the soles have stayed on over multiple short tramps and I have secured the midsole as well. Screws need to be just the right length which is a bit of trial and error.
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