I know oil paint would *not* come off in wetness, but it takes weeks to dry! So if you have some time and patience, because it's oil- and not water-based, it should stay on
You need to be sure to prep the rubber as well or the paint will not stick. If your boots are shiny you will need to sand them or use a chemical that will rough up the rubber. Not sure what type of paint would work. My answer is go to the Thrift Shop and grab a pair any size play with them and once your done you can put dirt in them and plant flowers. That way you aren't messin up your boots and have some funky planters too when your finished.
Even if you get the paint to stick, it will probably crack when the boot bends as you're walking. I've tried...and there are cracks in the paint near the ankle where the boot bends. The rest of the boots looks okay though...
It's different materials and everything, but I love buying old leather walking boots from thrift shops and using acrylic paint on them to do bright flower designs. The acrylic paint will come off in time, but you can always touch it up, and the boots are so cheap that it's fine to experiment xxx
I'd start with cheap latex paint (on a trial pair as enonomouse said) and you will need to create a texture for the paint to grab.
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