Normally ride in long boots, have never ridden in trainers or wellies! Have ridden barefoot both when swimming and when tipsily riding around the field bareback!
Have never ridden in trainers - can't think of anything more dangerous! As I have never owned or worn a pair of wellies I have never ridden in those either! I have however ridden in DM's, cowboy boots - love my Justins, CATS etc.. I do prefer to ride in proper boots made for the purpose though!
As for barefoot - well not quite - do sandals count whilst in shorts bareback on the beach and then swimming with the horse.
In summer I ride in my Kroops, but I dont allow them anywhere near the winter mud!
Winter I usually wear short boots, or wellies if I know I have to get on and off. Have never ridden in trainers.
when i was younger i used to wear wellies all the time, or trainers with chaps. not anymore! i now wear some amazing jodphur boots and chaps. A while ago though, i got on the back of a pony bareback with shorts and flip flops! went down to the river at high tide for a swim with the pony. I lost my flip flops! ahh what a summer
I ride in muckers and jeans sometimes (although very stretchy jeans I admit) but prefer to school in long boots. Don't like riding in jodphur boots unless with half chaps as I hate the no support on the ankle!