I found a pretty sweet solution. For Christmas I ordered him a blue blazer from Old Navy that is intended for a school uniform. Then I got him a pair of uniform blue trousers to match ... Well, they almost match. The whole set was about 25 bucks and he was over the moon about it.
He wore it for the first time the Sunday after we got home from our trip. If only he could figure out how to work with buttons. Once we get him dressed in this stuff, he can't get himself back out of it.
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