Answer:
Cheryl was proud of who her grandfather was either way and didn't care about her reputation as much as Martin does. Plus, her friends thought grandpa was great...On this day, Grandpa KNEW that Martin would be coming and he knew how Martin would want him to dress, so he dress accordingly..
Plus the fact that Grandpa wants to give the medicine bag to Martin because he believed that he was about to die and its the tradition of the family that the medicine bag goes to the oldest male child..