Carolyn Hax: What to make of a toddler boy’s preference for dresses?

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Adapted from an online discussion.

Dear Carolyn: My son is 2½ and loves dresses. Dresses on movie characters, dresses on toys, talking about who in his class wears dresses. He will wear my shirts and pretend it’s a dress. My husband and I aren’t really concerned about it, we figure we should let him pretend what he wants and play dress up the way he wants. And he’s right, dresses are pretty.

Although we’ve talked about it, we haven’t bought him a real dress-up dress to play in. Of course, family members have questioned the wisdom of “letting him pretend he’s a girl,” which we either ignore or shut down. But I do wonder about whether we’re supposed to be doing something other than what we’re doing.

To complicate things, he’s going to have a baby sister soon, who I’m sure will wear a dress or two. And he’s noticed that some people wear dresses and some don’t. We love him the same no matter what he wears, now and always, and my biggest concern is that he knows that. Is there anything else we should be doing? Should we just get the poor kid a real dress?

Wondering: Yes. But you can do that one better, just to honor his being a child and a dreamer and a person in progress toward you-(really)-have-no-idea-what: Throw together a dress-up box. Fill it with costumes, hats, props, capes, cowboy boots and, yes, dresses. Whatever you can afford or scrounge. Ask friends with older kids.

I’m glad you handled the “letting him pretend he’s a girl” thing the way you did, because I just … ugh.

Understanding that people are who they are no matter what we dress them in is the best thing you can do for your child here. So the rest is just details.

Re: Wondering: My elder child is transgender. Never wore dresses. Never played dress-up. My younger child was a tiger from time to time, roaring her answers to every question. Imagination is not destiny.

Parent: Too bad. I would be Underdog.

Re: Wondering: You’re doing great. Don’t let anyone push you into shaming your kid for his choices. My youngest is trans and when she came out, I immediately remembered a moment when she had put on her sister’s princess dress and been SO HAPPY until her older sister — who was under 5 — laughed at her and told her it wasn’t for boys, and she never put it on again. She doesn’t remember this but both her sister and I wish we had handled it better. And not wearing dresses didn’t make her cisgender.

Anonymous: And wearing them won’t make a toddler boy trans. Just dotting the i for those with yaps poised to open around a boy in a dress.

Other readers’ thoughts:

  • I love the way men in kilts look. There was also Billy Porter in his ravishing tuxedo dress at the Oscars.
  • Dresses are amazing! So comfortable and much cooler in hot weather. Honestly, I don’t know why men everywhere don’t wear them. I mean, nobody ever looks askance at my female self for wearing pants. Plenty of cultures around the world are perfectly fine with it, plus Harry Styles.



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