A young boy, wearing a jesters hat is enjoying himself sledding.
A boy wearing a goofy hat is sledding by himself.
Jesters hat is a goofy hat and himself sledding rephrases sledding by himself
A young boy is a boy of a certain age group. A jesters hat is associated with silliness and jokes so it would make sense to call it goofy.
A jesters hat is a type of goofy hat.