One thing i thought about with the PTO shirts is whether or not its a fund raiser of some sort. If it is a fund raiser and if the money benefits the school or the children (as opposed to coffee money for the soccer moms) i would think twice about stepping on their toes here. Maybe use this as a reason to change school policy like "we want every child to have a field trip shirt for safety and school pride so lets build it into student fees this year".

I remember my school sold school tshirts. You could wear them in gym class. Gym class was where you could tell the poor kids from the rich kids because half the class had white t-shirts on and the other half had these really cool school shirts. No one ever asked what the money went for. I assume its for the kids but it could have been for a coffee maker in the teachers lounge.

Setup an account here: http://www.youcaring.com/ I used this to help with Sadie's medical bills when i pulled her from animal control. Money was sent directly to my paypal account.

This way the donated money is being routed through youcaring so it doesn't look like income. It also gives you a "have they reached their goal" page so people know how much more there is to go.