"Mommy, why do you look so nice today? Can I wear lipstick too?" Yes, at home, I tell my four-year-old son, Ivan, but not to school till he's older. Makeup is for older people. "How old?" he asks urgently. I frankly have no idea, but say -- with pretend confidence -- that I doubt that our friend Selena, who is ten, is allowed to wear makeup to school. Ivan is skeptical that Selena lives under such a harsh regime: "She's a really, really big girl!" The funny – and refreshing – thing about this conversation is that Ivan isn't the slightest bit interested in whether he's the appropriate gender to wear lipstick. After considerable stress over gender roles – now familiar to Raising Trouble readers – he seems to have recovered a sense of freedom. And I think going to school with a boy who wears a dress – and with teachers who find this perfectly reasonable – has made all the difference. My friend Rachel says there's a boy in her kid's preschool class named Eli who wears dresses, too, like Iggy, whose fashion-forward sensibilities have been discussed here before. To explain Eli's unusual behavior, Eli's mom tells the other parents to tell their children, "He's a girl inside." Rachel doesn't want to tell her children anything so absurd. I wouldn't, either! I'm sure Eli's mom means well, but four seems much too young for that. Adopting a trans identity is a grownup decision. Also, telling other kids that a boy wearing a dress is "really" a girl sends them the conventional and wrongheaded message that boys can't wear dresses. By contrast, simply telling children – if they ask - that there's no reason why a boy can't play princess (wear dresses, carry a Dora lunchbox, etc.) if he wants, seems way more helpful. Iggy is most popular among the girls in his preschool class. When the girls have girly theme parties – including a "Diva" party in which everyone dressed up and did their nails – Iggy is always the only biological male invited. But the boys respect Iggy too. On a recent field trip to the New York Aquarium, they tried to impress him: "Look Iggy, there's a pretty fish! A pink one!" I think Iggy's example – along with that of Ivan's close friend Lee, a girl who will wear only boys' clothes, is obsessed with Spiderman and plays almost exclusively with boys – helps the other kids in the class to chill out and not worry so much about being "normal." In fact, the kids police each other's gender less than they did even a few months ago. After considerable conflict with his pals over whether boys can play with dolls – which led to extensive and brutal baby doll abuse at home – Ivan has started caring for his baby doll again, even asking if he can take her to school. A couple weeks ago, he nervously hid the baby in his backpack when we entered the school building, but the other day, he took her right into the classroom and showed her off. This weekend, he took her to the store, and on a long neighborhood walk. All in all, he seems to have recovered a healthy disregard for categories. "I'm not a kid, I'm a grownup," he said with a swagger the other morning, as he went to brush his teeth. "I'm a lady truck driver."