Sarah Rich in The Atlantic:
In hindsight, our son was gearing up to wear a dress to school for quite some time. For months, he wore dresses—or his purple-and-green mermaid costume—on weekends and after school. Then he began wearing them to sleep in lieu of pajamas, changing out of them after breakfast. Finally, one morning, I brought him his clean pants and shirt, and he looked at me and said, “I’m already dressed.”
He was seated on the couch in a gray cotton sundress covered in doe-eyed unicorns with rainbow manes. He’d slept in it, and in his dreaming hours, I imagine, stood at a podium giving inspirational speeches to an audience composed only of himself. When he’d woken up, he was ready.
He walked the half block to school with a bounce in his step, chest proud. “My friends are going to say dresses aren’t for boys,” he told me casually over his shoulder. “They might,” I agreed. “You can just tell them you are comfortable with yourself and that’s all that matters.” I thought of all the other things he could tell them. I began to list them, but he was off running across the blacktop.
I scanned the entrance to see whether any parents noticed us as they came and went. I hadn’t expected my stomach to churn. I felt proud of him for his self-assuredness, for the way he’d prepared for this quietly and at his own pace, but I worried about what judgments and conclusions parents and teachers might make. And of course I worried somebody would shame him.
More here.