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As an 8th grade math teacher, I can say that I typically have a couple boys each year that will grind out the Michigan winters wearing shorts to school each day. I do agree that it the choice often results from a need for the boy to push back on helicopter parenting. A way to say to 'screw-off' to over-protective Mom and Dad. The 'devil-may-Care approach to the weather often earns them extra coolness points with the kids around them.