This is a comment by Collin on the post “My Son Wants to Wear a Dress“.
I’d say find a decent place where he can wear a dress and let him wear one. I wore one a bunch of times—I thought it was really REALLY cool how when you’d spin around in circles it would “swoosh” out. I also found it awesome how easy it made going to the bathroom. No zippers, no buttons, just up and you’re good to go! With that said, you should probably still have the “boys don’t generally wear dresses and other people may look at you funny because you are” conversation if you want to do it.
I’m sure he is still getting the vibe that you don’t want him to wear one because of the telling him later. Or let him wear one around the house. If I were a more confident man, I would totally rock a skirt as an adult. It’s more comfortable and more convenient than shorts!
Photo credit: Flickr / breahn