I think it may be more cruelty than kindness to give into little Jack's desire to wear rain boots. They slow him down, trip him up, and inevitably fall off. Yesterday, as I was clearing the camp table of our breakfast mess, and the kidlings were playing outside the dining hall, one of our campers found me and said, "Your little boy lost his boots, and is walking around in the snow in his socks."
I assured him that it was nothing new or worrisome, and thanked him, and went outside to put the boots back on.
His socks were dry, so he hadn't been in the snow at that point, actually. He had been walking in the snow before breakfast, though, and did again after.