i did these shoes for a girl around age 5 who decided that she wanted a cat, flowers, a heart and banner, and wild horses...but they turned out cute all in all, done with paint pens on canvas vans old school slip-ons

on all of these shoes i used paint pens from Michaels and classic vans slip-ons
the pens work really well on canvas and last a long time, especially if you spray it with weatherproofing spray

its really pretty easy, if you have some basic drawing skills because the canvas takes to the paint really well and it will last for a long time if you take care of them.