Yea. Well in colonial America, people were very poor. I'm guessing shoes were expensive. I think Jack put his family first so they could have things. If you look at his sister, her dress was barely frayed and she had shoes. Jack's pants are tattered, he has bindings on his legs to keep them from getting more worn. I think he gave up his tooth fairy money, giving it to them. It goes to show you he has a warm heart.
I can totally relate to this! I love walking around barefoot outdoors regardless how dirty they get. My family would tell me to put some shoes on inside and outside the house. I can't help it, I love the way the grass feels in between my toes! hehe X3