My school has a HUGE anti-hat / hoodie issue as a means of respect for the school. Personally, I don't care too much, especially if a student is using a hoodie to hide the effects of homelessness, but I still try to enforce the rules. I tell my students, "Take your hat / hoodie off and stay a while!" In that way, I'm asking them to shed their shields and trust my care for a few hours. Additionally, if I see that a student is using that hoodie to hide abuse or something else, I can gently escalate my advocacy and see how I can help.