From 2006, this was the original design for the Holden Caulfield "Boom Box" shirt. Everything was done in Photoshop.
Here's the mock-up of the shirt.
In this final version, the printer called me an suggested that we change it to this so it was similar but easier and cheaper to print. I still really like it, just not quite as much as the original. Still, I can't argue with his logic at all.