I have been thinking about how to approach this post for awhile now. I just haven't been sure exactly what to say. But I want to get it out of my head because I think it is more helpful that way.
About 2 months ago, we found out my oldest son needed glasses. When we went to the store to pick out frames, my husband and I agreed that whatever he picked he could have because it meant he would actually wear them. It turned into quite a struggle because he didn't want to try any on. We eventually turned it into a game and he was focused on a pair of frames that had stars on them. They just happened to be pink. While my husband and I were trying to keep our younger son occupied and figure out what frames our older son wanted, the assistant leaned over to me and whispered, "Those are girl frames."
DUH. I knew that. They were pink, had stars and glitter, and had a well known kitty on them. I turned to the lady and said, "I know. But if it means he will wear them, I don't care." She looked a little taken aback at what I said. Kudos to her for accepting it and following my lead while talking to my son about them. He eventually settled on a striped pair that he now calls his "tiger glasses." But if he had stuck with the girl frames, you bet I would have bought them for him.
Now I'm sure some people reading this will say things like, "Don't you think he'll get made fun of?" or "He's a boy and you should dress him like a boy." Of course I worried that he would get made fun of, but if they were what he wanted, he would have defended his decision to his friends. Trust me on this, he is very strong-willed (and that's putting it mildly). I also know that very few kids would get close enough and pay enough attention to his glasses, so the odds of that happening are pretty low.
Now to address the other issue. Yes he is a boy and he dresses like a boy; that's what he picks. But my boys are also fans of Doc McStuffins, Sophia the First, and some other shows that are geared toward girls. If one of them decided that they wanted a toy or a shirt that was one of those characters, I would buy it for him. I take the approach that my grandma had: every boy should have a doll and every girl should have a truck.
I have read stories about boys being teased for dressing up in girls clothes to play. It's interesting that it doesn't always go the other way. If a boy dresses like a girl, he's labeled a sissy. Sometimes people even think he might grow up to be gay. If a girl dresses like a boy, she's a tomboy. Sometimes people might think she'll become an athlete. So why does it make a difference? If I had the answer to that, I would be rich.
I want my sons to be happy. It took me almost 30 years to figure out what I wanted to do with my life that would make me happy. I hope they figure it out sooner. But will I be upset if one of them wants to dance instead of play football? No. Will I be upset if one of them wants to be involved in theater instead of basketball? No. As long as they are doing what they want, I don't care.
You don't have to agree with me. Parents can do what they think is best for their children. Just don't force your values or gender roles on your children if they choose something else. Let them be kids and let them be who they are. Everyone will be happier for it, and guess what? It's OK.