"After a while... wearing shorts when it was cold out became something he had to keep doing simply because he was already known as the Boy Who Wears Shorts."

"'There were days that got below zero... but it wasn’t even really a choice at that point... It’s like, if you’re going to wear shorts when it’s 30 degrees out, you have to be ready when it’s -10. This is your time to shine!'"

From  "The Boys Who Wear Shorts All Winter/The kid who refuses to wear pants is a familiar sight to parents, students, and educators—and a mystifying one. What’s so great about being underdressed?" and quoting Tyler Wood, who is now 31, but wore shorts year-'round in Boulder, Colorado when he was a middle-schooler,

I'm linking to this because I don't want you to feel I've missed it and you have to tell me about it. I know I'm The Blogger Who Writes about Men in Shorts. But do you see the word "men" in that article title? The word is "boy."

I have no problem with boys in shorts, and my problem with men in shorts is that shorts are infantilizing. Especially when they are baggy and worn with a boxy T-shirt, they make men look like enlarged boys. I realize that self-presentation as an enlarged boy is a matter of personal choice, but I don't think most men in shorts are trying to say, through fashion, I am an enlarged boy. I think they're simply doing what is easy and comfortable for them, and at most, expressing the idea that they don't care how they look and don't care if anyone finds them attractive. I'm just providing information. Make your own choice.

Now, for parents who worry about their sons suffering from the cold: I would lean towards letting teenagers wear what they want, but if your kids are younger, you have to protect them from themselves and you have to protect yourself from the intervention of Child Protective Services.