We have four boys, the youngest is a set of almost four yr old twins! We have a book that is buttoning, tieing, zipping, etc... I just gave it to the twins last month. They play with it and know how to zip and sometimes button. My husband taught them the bunny story for tieing but they get mad when tieing. Our oldest (now 12) received the book as a gift and didn't learn to tie until he was 5, our second son finally got it at almost 6. So everyone is different, just don't get mad or show frustration when teaching. You could find a book with these things or use a pair of his shoes to "practice" on. Just make it fun. Good Luck!