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What you said here makes sense, but I was referring to the FDR photo where the little boy was deliberately dressed up as a little girl for the photo. That seems different than what you were saying about how children of both sexes would be given dresses for pragmatic reasons.
Easily explainable. Different fashion back in the day.
A great example would be to look at what aristocrats in the middle ages used to wear back in the day. Men wore clothing that were peppered with garments, fancy trims with embroideries of all sorts of colors that would be deemed feminine now. It wasn't weird to see party clothing adorned with flowers and patterns to make them look like peacocks during parties. That overtly fanciness obviously carried over to children's clothing and it lasted throughout the ages. In the last century, there was a fashionable push for boys to wear more masculine clothing so the trims slowly faded out and a certain set of colors were popularly acceptable and everything else was rejected.
FDR picture simply tells you that back in the day the trims were still in fashion for boys and girls. The dress was white (very usual and easy to clean cause they would bleach the living shit out of it). He wore long hair but that was also the fashion. I believe they didn't cut boys hair until they were a certain age (and parents thought their kids looked super cute with long hair). Shoes look femine but again, it's a kid. It was definitely the style for kids back in the day.
You look at this and you think "oh they dressed him up like a girl". I don't see that. It was simply the fashion trend back in the day when people were less judgmental. They didn't care whether a little boy wore pink or had trims in their clothes and fashion was more free.
On a personal note why does it matter what a little baby wears in terms of color? Why can't a little baby boy wear pink? Suggest that to an average guy and he will look at you weird and ask if you are tring to turn that baby gay. Or is it because we are so lazy we can't be bothered to ask what the sex of the baby is and are relegated to color coding our offsprings? Sounds really stupid. Why can't he wear a fancy set of clothes with trims to make him look super cute and not have others judge him or his parents? It's absolute nonsense for anyone to believe that dressing a child differently will affect it. No it won't. But mocking him for it will. but why? Why do people want to limit themselves fashionably because some random people in the fashion industry back in the 1900s decided "you know what? all boys should wear blue and girls wear pink and that's that..". I find the concept a bit silly.
Anyway if you want a more thorough read on children fashion throughout the ages this is a short one that's not too bad:
http://fashion-history.lovetoknow.com/fashion-history-eras/history-childrens-clothing