Looking at the picture I'd say you could do it with a sharpie marker and it would look store bought. �Just outline it with a pencil and a ruler and use a fine-tip sharpie. �That permanant marker will hold up in the washing machine as long as the shoes will. �
I know what you're saying about the kids shoes being expensive and not lasting. �I'd say my guy outgrows his shoes in about six months. �They want to charge $30 for a decent pair of shoes for a little kids these days that are well made and won't hurt his little feet. �Hooray for Burlington and the 1/2 price rack!
It looks like a simple enough pattern if you have time to copy it and trace it. �I don't think you could use an iron on transfer on shoes.