The narrative follows the life of a young nobleman who lives for centuries, undergoing a mysterious transformation of gender while remaining the same person at heart. Orlando begins as a sixteenth-century courtier in the reign of Elizabeth I and persists through the Victorian era and into the twentieth century. The protagonist seeks to navigate the shifting social expectations of gender, class, and artistic expression across these disparate eras. The narrative framework employs a playful, mock-biographical tone that frequently breaks the fourth wall to address the reader directly about the challenges of documenting such an unconventional life.

This work is widely regarded as a seminal exploration of gender fluidity and the limitations of biographical form within modernist literature. Readers often note the wit and playfulness of the prose, which contrasts with the more somber tones found in other works of the period. The text is frequently analyzed for its radical subversion of historical conventions and its ahead-of-its-time treatment of identity as a construct. It remains a central point of discussion for those interested in the evolution of the novel and the intersection of history and fantasy. The book continues to be studied for its innovative approach to character development across centuries.