Sometimes, iron-on transfers just don't work (first photo). It started to crack almost immediately. I got one wear out of it. So, I peeled it off (two rounds in the washer/dryer then used packing tape to pull off the transfer) and tried again.
This time I used fabric markers and traced the design. I changed the style of the word "Hole". Admittedly, the ink came out of the wash more faded than I had hoped, but I think the image will stay.