One day I forgot to take my rain boots off and ended riding in them....luckily it was not a lesson.Half way through my ride I realized I was wearing them.A while after that I just rode bareback.It is kinda dangerous because your foot can get stuck, but you should try it out.Hopefully this helped!
Yes I quite like it a lot for some reason it was interesting I say give it a try
I haven't, but I don't think I would try. Your foot may get stuck in your stirrup because of the rubber material and because rain boots tend to have a wider sole than actual riding boots. It's best to only ride in boots that are specifically made for riding, doing otherwise could potentially be dangerous.