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A shirt would be horrid. I was thinking more about a license plate holder or bumper sticker. Something small yet easily viewable by others. If it's going to be clothing make as inconspicuous as possible. Maybe in the color of the school with a tiny logo.
In theory I agree with both you and rockket, but my feeling is also that whenever parents are shelling out $40K+ to put their kids through school, I give them free license to wear whatever the hell they want (haha). I'm sure that some Harvard parents have so much money it doesn't matter, but these probably aren't the ones who are wearing those shirts. It's the ones who are still driving the minivan instead of the Lexus that they could have bought for that tuition money to send their kid to Harvard/Princeton/Chicago/Columbia.