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 him and who might later tease him.
If we were going somewhere outside of the neighborhood where only strangers were around, and only strangers would see him, then sure, why not?
However, my 2 sons never wanted to wear dresses, so it...