They are all grammatical, but 3 doesn't make good sense. Babies aren't able to dress themselves! I'd write this:
You should have put the shirt on the baby.
1. You should dress him up.
2. You should make the baby wear socks.
3. You should have the baby put on the shirt.
4. You should have the baby dressed.
(Are they all grammatical? Do we have some more expressions similar to Sentence one?)
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