A man who wears glasses, a blue shirt and a Chicago White Sox cap holds a young boy who also wears a blue shirt.
A man is wearing glasses and a baseball cap.
Man who wears glasses is a rephrasing of man is wearing glasses.
Wears glasses is a rephrasing of is wearing glasses, and Chicago White Sox cap is a type of baseball cap.
A man is wearing glasses and a baseball cap (Chicago White Sox cap) as part of the total description.