My DS had crawling shoes bc of slippery floors so when it came to proper walking shoes he was fine, however we bought him some wellie/snow boots to go outside in and he refused to stand and pulled them off, we just kept putting them on and tried to distract him with a fun toy or game.
Also we made him as comfortable as possible, by this I mean my DS loves to be undressed and hardly ever wheres trousers round the house so we stripped him to his vest/onesie and put the boots on this seemed to work after a couple of tries and now he will wear his boots whenever we go out.
HTH and makes sense
Love