previous post hereThank you to everyone who replied; your responses were so helpful. We decided the best course of action would be to not really remind him about the dress (because it's not like we do that when he gets new clothes anyway), but if he asked to wear it, we'd let him. Today he asked to wear the dress to a playdate. The playdate was going to be indoors, so there was no compelling practical reason to say no. After getting dressed, I explained that most people think that only girls can wear dresses, so someone might say something that isn't very nice or might tell him that he shouldn't wear a dress. He looked sad, and I said that if anyone says anything like that, he can tell them that boys and girls can wear whatever they want. He said okay and happily went on our playdate.Well as soon as his friend (a 5 year old boy) saw him, friend immediately told me that [child's name] looks weird, that he's dressed like a girl, that he shouldn't be wearing that. Friend asked me if we had any other clothes and if my son could change. I explained that my son was wearing a dress because he wanted to and that he likes it, and that even though he had shorts and a t-shirt on under the dress, he wanted to have the dress on and wouldn't be changing. Friend's nanny took him aside at several points to explain that it isn't his business what other people wear (among other things), but he kept it up throughout the playdate - asking my son if he wanted to change because he shouldn't be wearing a dress - and by the end, did not seem interested in playing with my son at all (my son didn't really seem to care at this point, as he was happily playing by himself and with his little sister). Finally, as we were leaving, friend made another comment about the dress, at which point my son threw up his hands and said, "but boys and girls can wear what they want!"After leaving, an older woman told my kiddo that she loved his skirt and that the colors were beautiful, so he said thank you and did a twirl to show her how it spins. He was very happy. On the drive home, he asked to take the dress off because it was getting hot and uncomfortable. So he's learned a couple lessons about dress-wearing today, hahaha.Overall I was really surprised - both by how little I cared about taking him out in a dress and that the only negative comment we got was from another little boy; comments on my previous post suggested that adults were more likely to be shitty about a boy wearing a dress, so I was really shocked when this other little boy came out the gate swinging with "your kid looks weird." I'm happy that my son stood up for himself, and after we were home he said that he enjoyed showing off his dress, so I don't think his friend's negative reactions have hurt his feelings. Going forward, we will let him wear the dress when he asks if there's no good reason to say no (like a dress is impractical for gymnastics and soccer practice, the dress is dirty, etc), until or unless it seems to be affecting him negatively emotionally, at which point I assume he will stop asking to wear it in public.tldr: boy wears dress, other children are terrible, boy learns dresses have practical downsides but still loves them via /r/Parenting http://bit.ly/2XYWJUe
