Hi there. Trans woman with an opinion here.
Thanks for the article. It was thought-provoking.
How about trying this… Please re-read your article and every time you mentioned your son’s stated desire to wear a dress replace that notion with him expressing a desire to find a nice boy to marry when he grows up. And then see if your advice to yourself would be the same. That you’d tell him he could date a boy later. That he could have his boyfriend over when you knew you weren’t going to be going out so much for a time. And so on.
I have two daughters. I know what it is to worry for them. Likewise my wife worried for me when I came out as trans. But there’s only so much you can do to protect the ones you love on the one hand, so you have to trust that they have the ability to look after themselves, which is basically the job of parent in only a few words. On the other hand protectiveness is only ever one word or action from overprotectiveness. And that’s a slippery slope because in our zeal to shield a loved one from the cruelties of the world we can too easily as that they curtail who they are to minimize the risk. I know you, as a gay man, assuredly know what I’m talking about. Closets are often built by well-intentioned hands.
You mention not wanting the world to teach him shame. You do realise that you’re doing their work for them? That your article is littered with shame regarding shifting gender expression. That you don’t mention transgender or gender non-conforming people but do mention drag perhaps says something. I’m tran. I’m not ashamed. But I was. And it started at home.
So maybe instead of stopping your son wearing dress to the playground let him. Be on hand to step IF needed. Otherwise let it play out. If he encounters a negative reaction he will (or will very soon) be able to decide for himself if wearing the dress is worth the hassle. And it’ll be his call to make. If he bins the dress, whether it’s cos he’s cis and it’s a dalliance, a phase, or if he’s trans and wants to climb in the closet for a few years, that’ll be his perogative. Likewise if he keeps wearing it, despite other kids’ (and parents’) disapprobation, then you can be sure it means enough to him. And his reasons are HIS, not yours. Oh and those parents? Yeah got to town. They have less than no right to police your child.
You should be so proud that at that early age he knows what he likes, rather than looking round at what others are doing/wearing. Cultivate that iconoclasm, don’t quash it.
And even if your kid isn’t trans (yeah still damned unlikely) his gender non-conformity is helping in changing attitudes, and making the world in general safer for trans folk. Much love, many hugs