Apparently the dragon like logo on the face represents the Jabberwocky from Alice in Wonderland! In 1888 two girls at the school decided to start a school newspaper and chose the name Jabberwock. They wrote to London to ask Lewis Carroll for permission which he granted in a hand written letter. How exciting that must have been for those girls!
You can read more about the story here on the Boston Latin Academy website. And the ring is available here on my Etsy site :)