School Clothes - boy style

I have another child entering the public education system. This time a boy, and one who really could probably care less about designing his own clothes, like his sister. However, drawing his own designs (one from and Ed Emberly drawing book) and having his mom stitch them onto his new Tee's? Very interested.

Edit: to transfer his drawings I used a tracing wheel and transfer paper, available at every sewing store. And if you aren't sure what it is, just ask a worker. The paper transfers a light, chalky line. I also ironed on fusible interfacing on the underside of the shirt for support while I stitched. L reports this as a little itchy, so he'll be wearing undershirts with these shirts.

Edit 2: If I had it to redo, I would use the lightest interfacing available - I'm regretting the heavier weight that I used. And actually what I would do is first stitch on the design, then iron in interfacing to protect the stitching and knots.