My entire life, I've had a problem with boots. I can find shoes that fit perfectly and I can wear all day in all conditions, but when I wear boots, I >always< get very painful cramps in my right foot in the muscles where my "ring finger" toe (aka the toe next to my pinky) attaches to my foot.
I don't now if it's something about the high tops around my upper ankle, lower leg, but this is something that makes all outdoor camping and hiking a literal pain. As I say, it has happened my entire life. When I was in Scouts, I couldn't go half a mile without having to stretch my toes. In the military, I was in pain all day when I wore boots. People always told me I was just trying to get out of work or effort or whatever.
Has anyone ever heard of this?