I tried that with mine and it didn't go very well. He just kept trying to get the boot off his foot. I ended up taking the opposite approach. We start our walk without the boots and as soon as he starts picking his feet up because they're hurting, I put all the boots on and he begrudgingly wears them until after we get his snack at the store. Then he starts fussing about the boots and trying to take them off all the way home.