I use either runners or ex work boots depending on the terrain and season (snakes, water etc.). I would like to try moccasins one day, but I hunt a lot of rocky/prickly terrain, and like WB I'm a degenerate (though thoroughly unmodern
) man. A family friend used to go shoe less year round here and mowed grass for a living for part of his life - he had soles like rock hard leather!
Ankle supporting boots can be handy if you're carrying a lot of weight and/or hiking in rough terrain, but since beginning my Alexander Technique journey, I've found that better (or proper) body use and some forethought will prevent a lot of injuries.
Steve