Shoes on babies

My son can walk, he is almost a year old and he has been walking around for over two months by now. Till now we have had him barefoot inside and we use Liliputi barefoot shoes outside. These are basically like leather slippers and my son loves them. The down side is, they are not water proof and fall has come. We have tried wellies on a rainy day, we have tried some other boots, that are not barefoot shoes. But. He just sits down and avreams until we take the shoes off. Shoes fit him, so that is not the issue, but regular shoes are a bit stiff...

How can i get mu son used to boots? I can't have him barefoot outside anymore. ☹️