Today was the first day of school, and school is so much better with students! I decided to let hats in the classroom. About three students took advantage of the allowance. I'm ultimately glad I did because I think it showed my students I am willing to figure out where they can have choices and where I need them to follow (a useful life skill, always).
School isn't working for a lot of students. They don't put school in what Glasser calls their "Quality World" (which is just a fancy way of saying that, for some students, educators haven't done a very good job of showing students why and how school matters. If it takes wearing a hat to let a student know that this is a place where he or she is welcomed, I'm willing to let that piece of my culture go. I trust that as we all work to show students that we have their best interests and hopes and dreams in mind, they'll listen when we say you shouldn't wear a hat to a job interview (or a job).
Ultimately, I took my direction from other teachers on my hall who know the school culture better than I. Nearly all of them allow hats. Nearly all of them seem to enjoy very meaningful relationships with their students. And all of them have students who go on to be very successful in a variety of ways. With and without hats on.