Does anyone have any recommendations for comfortable calf-length leather boots? Does such a thing exist? I'm reluctant to fork out for a pair only to to find out that they shred my feet, as tends to be the case with footwear. Oh, they also have to come in a size 9 for my massive feet!
I ordered a bespoke pair from The Bootmakers (Balmoral, black, flat) and their cushioned soles are as comfy as trainers. Walked about 10 km in them today. And I wear an 8/ 42 in them. Not cheap but the best footwear investment ever.
I have a pair of these, and I have genuinely worn 5-6 times a week for the last 2 years, they are super comfortable. However these may not be as high as you were looking for, I have my eye on a pair of these as my new winter boots!
They are not going to be everyones cup of tea but I have a pair of Dr Marten Phoenix Jara biker boots. They were like a pair of old slippers from day one and are going strong 3 years down the line. I don't drive either so walk a lot.