I'd be somewhat tempted to keep them if they were my size, even though I was never a Game Boy owner myself (just gotta love the retro design of the shirt and the cleverness of the whole shirt becoming a Game Boy). I appreciate the commentary on iPods in the first shirt. :)
Luckily not everything is my size, or my t-shirt collection would be out of control. I did buy and keep a vintage 1990s Mr. Bean t-shirt for $3 this week!