I like the way he's advertising his intelligence from day one!
As to the teacher. Ok, I don't want them to all look frumpy wearing odd sweaters with animals embroidered on them and horrible pants with socks and old fashioned nursing shoes...but still. How on earth does she intend to run to a kid if he falls off a swing and breaks his arm? She'd break an ankle on the way there. Plus, if she's requiring you to be extra familiar with her if she's leaning over, doesn't seem quite the thing to do when there are short kids in short desks that are probably going to be behind her with a great view of her behind. If I could get away with wearing her outfit I sure as heck would, but I wouldn't be bending over with kids around.