Oh I'm sure the guys would love it!
I'm not sure how close you've paid attention to FAA/NATCA contract stuff, but we just got a new contract which allows us to wear normal street clothes to work. Pretty much anything goes except nudity/swear words etc. I'm pretty sure management would take it as an opportunity to stick it to the controllers.
You hit it right on the button with the shirt, providing those extra services (VFR flight following mainly) can be a real PITA when you have a bunch of sectors combined up on a busy Sunday morning, especially when grandpa in his Grumman Tiger with his crappy radio wants to tell you his life story.
