I was reading through my new book by Alison Smith and there is a whole 2 page spread on sewing on buttons, both shank and holed. The 2 little girl dresses had buttons of both kinds. The pink are shank and the blue ones had 2 holes. I had never thought about placing a toothpick or pin in my case behind the button to give the material room to lay flat behind the button. I think a toothpick would probably work better to allow room because they are thicker than the pin I used. I also did the wrapping stitches around the looped ones. It is rather sturdy and will hopefully last quite a while. I just happen to see a tutorial on button sewing today at the Sewaholic blog. It is quite good. Basically done just like my book says to do it.