- Childhood: Silverstein's poems and drawings often captured the innocence and wonder of childhood, as well as the challenges and frustrations that kids experience.
- Humor: Silverstein's work was often humorous and lighthearted, with a sly wit and a penchant for wordplay and absurdity.
- Nonconformity and individuality: Silverstein's characters often celebrated non-conformity and individuality, and bucking societal norms.
- Friendship and family: Silverstein's work frequently explored the themes of friendship and family, and the importance of love and support.
- Social commentary and satire: Silverstein's work also included social commentary and satire, often poking fun at societal conventions and norms in a playful and thought-provoking way.