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?)

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.

Yes, all of the sentences you provided are grammatically correct. They are all imperative sentences in the form of a suggestion or recommendation.

In terms of expressions similar to Sentence one, here are a few examples:

- "You should dress him nicely."
- "You should dress him in something formal."
- "You should dress him for the occasion."
- "You should dress him up smartly."

These expressions convey the idea of dressing someone in a manner that is suitable, appropriate, or stylish.