Did you sleep with that clothes on? Do you want to eat with that clothes on? How about Do you want to wear it while you are eating? Do you want to wear it and eat?
Will these fine to say?
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Top answer
"clothes" is plural: Did you sleep with those clothes on? Do you want to eat with those clothes on? Or: Did you sleep in those clothes?
— GPY
"clothes" is plural: Did you sleep with those clothes on?
Do you want to eat with those clothes on?
Or: Did you sleep in those clothes?
Do you want to eat in those clothes?
The second one obviously requires a situation where there may be some question about the appropriateness of the person's clothes.
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