Hats are not allowed at our school, so in an ideal world, no students come to school with hats, and if they do, they politely and compliantly take them off when a teacher points it out to them.
I've had various degrees of success with this. What's working for me now is, "A hat in school? Let me see your hair, I bet you have great hair ..." and then I make sure to whistle at their mane when they take off their hat. This works most of the time.
Well yesterday, I was doing a duty in the main hallway, and a teacher was basically screaming at a student at first meeting about his hat. Really screechy like. Blach. The kid, you could see was a good natured kid, and he'd just come in from outside where it was cold. Basically the second sentence out of her mouth was about reporting him to the SRO (security officer). I mean, it's no wonder the kids are highly suspicious of adult interactions.
During my first period, a big football player type of kid comes in wearing a pink, striped shirt. A friend walks up to him (a girl) and hugs him and says it's a great shirt. He smiles sheepishly and said he had to wear it because his girlfriend bought it for him.