A young nobleman in the Elizabethan era undergoes a mysterious transformation that spans three centuries of English history. Orlando begins as a male poet in the court of Elizabeth I, seeking meaning through literature and love. As the narrative progresses through time, Orlando shifts gender and experiences the changing social expectations of the eighteenth, nineteenth, and twentieth centuries. The narrative framework employs a playful, mock-biographical tone that mimics the conventions of historical record while subverting them through fantasy and irony. The protagonist remains the constant observer of these shifting eras, navigating the constraints of class, gender, and artistic expression.

Readers and critics frequently highlight the inventive prose and the playful, satirical tone that distinguishes this work from more somber modernist texts. Discussion often centers on the fluidity of the protagonist's identity and how the narrative challenges rigid societal norms regarding gender and time. Many observers note that the book serves as both a love letter to Vita Sackville-West and a critique of the biographical form itself. The balance of historical detail and whimsical fantasy creates a distinct atmosphere that remains a focal point for academic analysis. Readers often find the shifting perspectives on history to be the most engaging aspect of the reading experience.