SageMother

If you are reserving a special pair of shoes for play, then make sure they are easy on and off. If he can't tie them then they need to have Velcro so the teacher isn't stuck with the responsibility of changing his shoes for him, which isn't really her responsibility at all.

If he is sensitive about his appearance, then you might simply have him wear scruffy shoes to school all day and keep his nice shoes for other occasions. I know this seems harsh, but if he isn't treating them in an acceptable fashion, providing him with a way to escape the logical consequences just perpetuates the problem, which may generalize to other objects that he needs to learn to take care of. I have no studies to back that up, mind you.