Thank you Hebaragi. If it is any consolation to you and your son, my oldest (#1) arrived at West Point having lived in the tropics for most of his life (the real, far side of the world exotic sort of tropics). The good news is that they are issued clothing and told what to wear in the varies different types of weather that occur when you live in a country or location that has actual 'weather'. While he was never one much to complain, in February of his plebe year, #1 said, "I had no idea it could be this cold for this long and that it hurt." Can Colorado Springs be as bad as Hell on the Hudson?
There is no discouraging teenagers with the threat of inclement weather! Good luck. Does he own pants/slacks? That would be a good place to start...