I remember studying the Tinker v. Des Moines case in law school. The professors made it quite clear that the Supreme Court decision upholding the right of students to wear black armbands in protest of the Vietnam War was a noble moment in the history of free speech. I pretty much yawned - something I did a great deal of in law school - and went along.
Having been in the real world and studied organizations, however, I now have a different take. I think it would have been wiser if the Court had accorded greater discretion to the school administration to control such conduct. This is not because the administrators would decide wisely (let's not get carried away), but because they have a school to run. School administrators should not be expected to be constitutional lawyers nor should they live in fear of being dragged into a costly lawsuit because they made some minor decision to promote order and discipline. There are moments when the person on the ground should be given a reasonable level of discretion.
Micromanagement by courts, of course, is one of the Halloween stories of our time and the threat is all too real. I see company executives who adopt rules that defy common sense, but which will protect them if a lawsuit arrives. These rules almost invariably have an automaton nature to them. The willingness to make a "subjective decision" - as in one based on years of study and experience - is squelched out of fear that the hapless decision maker will be put into an emotional meat-grinder and then grilled by an advocate who's never had to run an organization. That unseemly concoction is spiced by the sense that career-conscious higher-ups will quickly back away from the person who made the tough calls.
I'm not sure how much liberty the removal of discretion has provided, but I know it has created a definite climate of fear.