In today's public secondary schools, administrators face challenges that prior generations never anticipated, one of which is the T-shirt conundrum. The T-shirts that students wear to class contain all sorts of messages and images, many of which administrators may well consider inappropriate. This article is intended to help beleaguered educators sort out which messages and images are protected by law and which may be censored by administrative disciplinary action. Recent controversies are examined through an overview of federal court rulings. The article then concludes with some practical guidelines for educators and school boards.