Super comfy, stays warm, Haven't tested the waterproof part yet but we didnt get these for that. But, because they are high top shoes, if you walked in snow or rain you'd probably end up with some sort of water through the top of it isnt secured correctly woth pants or something. Either way, My brother has always hated going barefoot and loves these style of shoes, along with the regular walking shoes, they've helped him confidently go barefoot more often.