We did this last year. I think it looked adorable. I just put these two images together in an attempt to show him how nice it looked. No dice. Right now it's longer than in the picture on the left. And apparently it needs to stay that way. Why?
1) When his hair doesn't cover his ears, his ears are "too windy".
2) When his hair doesn't cover the back of his neck, he shivers. All the time.
3) When his hair is short, it doesn't cover his face when he sleeps and his face feels naked.
Maintenance isn't fun - washing, detangling, combing, etc. But if the long hair makes him comfortable, I can deal with it. I think I'll just hold on to the short hair picture and look at it from time to time :)