If I had a son, I wouldn't be ok with him wearing a dress either. Children have plenty of other ways to express themselves and I don't see anything wrong with teaching them that some things aren't socially acceptable or appropriate in certain circumstances. Likewise, I don't allow mine to wear a winter coat in scorching heat or sleeveless dress with nothing else when it's cold, knickers on the head in public, my bra, high heels, make up, nail varnish, toilet roll scarf etc. If she wanted to go out naked, I wouldn't allow it either. To me, it's not any different from say not allowing excessive amounts of sweets (no matter how much she wants them) or draping spaghetti on oneself in a restaurant. The culture and tradition I come from, and live in, don't view boys wearing dresses as appropriate or socially acceptable.