Would you be okay with your young son wearing a dress?

Yes. You're not the one who is wearing the dress. Even as the parent of your child, you've got no right to dictate how your child chooses to express themselves. It's self-centered thinking. Let your child wear whatever the hell they want, you don't know how they're truly feeling or what they're going through. I can't believe we have to debate something like that. If everyone got off their high-horse and realised that other people don't have the exact same set of values as them, the world wouldn't be the shitshow that it is today.

I say yes because I don’t care. It’s just fabric. I can’t help but look at it from a cultural and fashion history perspective, as I think our perception of what’s acceptable for males is still narrow compared to everything they have ever worn. And in recent times girls have been given more leeway regarding what they can wear, even celebrated as “low maintenance” for being tomboys. I do not automatically associate expression with gender identity. If the expression is however to represent identity, that is fine, but that’s also something that can take a long time to be sure of. I would just assume let them play and figure things out in time than make a big deal out of it. 

While I do logically understand why parents don’t want their child to be subjected to bullying or general unwanted attention, I can say from personal experience that it does not work. At least beyond physical safety concerns. I always knew when I was putting myself in the line of fire, though I could see gently informing your child to make sure they are aware. But my parents not supporting me, in the name of protection, felt invalidating, almost like saying people would’ve had a good reason to give me a hard time. When you’re “weird” it doesn’t matter what you look like anyway. 

Short answer: No
Long answer: No

Yes - anyone should be able to express themselves through their clothing. And, I believe everyone should be able to feel comfortable with what they are wearing.

I don't see why not, it's their choice after all and they will be the person wearing it.