In preschool, elementary, and middle school there were the occasional theme days: pajama day, crazy hair day, and of course Halloween; my son often balked at these, not inclined to go along with the crowd. Last school year, his first at a large public high school, he participated in “Spirit Day,” dressing up as prescribed by a group of seniors to demonstrate school spirit. (Although it seemed more like hazing to me.)

To be fair, my son has paid attention to fashion for a while. As a first-grader, he saw an older boy with long hair and said “I want that…” And from first through eighth grade he grew his hair out to a very long length. Known as ‘the boy with long hair,’ and often mistaken for a girl, he added to the persona by dedicating a year of his life to wearing only tie-dye. Notoriety followed these fashion choices, and many kids in the school followed suit, growing their hair and mimicking his style. My son played it cool, never seeming to be too headstrong, he remains down-to-earth. His tie-dye shirt collection even drew a nice bid when auctioned off at the school fundraiser.

The hair came off just before high school, and his fashion changed from hippy to hipster, with ironic t-shirts, five-panel hats, and loud Van’s skater shoes. Still a leader in the fashion arena, his jeans got skinny and shirts bright and flowery. All of this remains consistent with the gender fluid identity of my son and his friends. “Queer” is de rigueur and it makes sense to dress the part.

So as the new school year approached, our son began gearing up. His store of choice is Buffalo Exchange where flowered shirts, short shorts, and ironic tees abound at reduced prices. We buy all but the most garish garb for him, feeling compelled to clothe our son as we strive to accept and support who he is. A couple of purchases he made from his own funds were dresses. We assumed these were intended as costumes for his avant-garde theater group.

But last evening, after describing his first day of school sophomore year, he casually announced that on day two he’d be wearing a dress to school. His mom and I didn’t miss a beat, merely curious why he waited for the second day. “Doing it on the first day would’ve been such a cliché!” was our son’s response.

And so this morning after a shower, and applying the subtle eye make-up that’s been a daily routine since he appeared in his first stage production last spring, our boy donned a dress and packed up his book bag before classes.

The blue cotton sundress he chose would be fitting of any teenage girl. Heck it might actually be something his mom would wear. And he looked pretty darn good in it. I like how it ties behind the neck, and I wondered how he got it on without asking for help. The unfilled bulge at the breast is a bit distracting at first, but overall he looks like a fit young man making a bold fashion choice.

These are the types of choices he’s making, and as a parent I am strongly compelled to leave well enough alone and let my son navigate his own course. That this path leads through the halls of a big urban school is something he must’ve calculated. That he’ll be in the company of familiar friends, and under the eye of new teachers and administrators, may have figured into his calculations.

And when I check my own feelings, I need only recall myself as a high schooler, seeking attention and acceptance. My persona was as a merry prankster (in the Ken Kesey tradition), a yippie letting my freak flag fly with bright clothing and bold public actions. Later, my academic career centered on gender identity development and it seems only fitting that my son is exploring similar territory, and taking it to new places.

“Nice dress” was how I greeted my son this morning. “Thanks” was his reply. “I’ll see you after cross country practice, at the back-to-school picnic,” I continued. “Cool” he said.

And cool he is, with the whole idea of a not-yet-sixteen-year-old boy going to school in a dress. I’m cool with it too.