Inside our house? sure.
In our yard? sure.
Outside in public? yes and no, it depends.
I dont think I would let him wear a dress out of the house, in our neighborhood down the street where people or other children might know...
I have 3 children, and never made any of them sleep if they didnt want to. They will sleep if they are tired. Never ever had a problem. I cant imagine if someone tried to make me sleep if I was not tired.