: He will be O.K. Even if his feet hurt, he will not complain, especially around his mother.
I walked all over England, Scotland and Wales wearing cowboy boots on a summer trip while in MY teens. The only problem I encountered was an occasional calf muscle crap during the night after a long day of touring. Don't remember getting much reaction from the locals re: my boots, but then I wasn't as "boot aware" as I am since finding this group of folks.