My 2 year old son likes dresses. Pink ones, white ones and orange ones like the one here. He watches his sisters dress up and undress many times a day. Why shouldn't he join in? I don't have to worry about my children being mercilessly teased because they dress how they like. If I am going to be honest I may have an issue with my almost 6yo wearing a dress out. If he insisted I would tell him what reactions he may get and let him decide from there. I want to equip my children in this world but also allow them to self express. Fine line.