Why does Dill's explanation of Jem's state of dress almost land him in trouble?

Is the "almost land him in trouble" referring to Dill or Jem?

Thanks.

It could be either, it is not clear.

If the first names were clearly masculine and feminine, then the "him" would refer to the masculine person. However, I cannot be sure of the gender to either Dill or Jem.

In order to answer your question, I need some context. What specific book, movie, or story are you referring to? Once I have that information, I can explain how to get the answer to your question.