Have to keep shoes on my horses that are playing/in training, because the heel caulks help grip the surface and keep the horse from slipping. My horses in pasture are barefoot, and I would do basic arena work without shoes... but because SoCal is so rocky, I wouldn't go barefoot on the trail. Especially not with my TBs (although two of the four have very hard, big feet) - maybe with my Teke? I should invest in Boa boots. Do you find that they chafe around the ankles at all?