If you were captivated by Orlando's fluid approach to gender and its whimsical, centuries-spanning narrative, you'll love The Passion. Winterson follows Henri, a French soldier, and Villanelle, a Venetian woman with webbed feet, as their stories weave through war, love, and the blurred boundaries of identity. The novel’s magical realism and inventive structure echo Woolf’s boldness, inviting you to rethink what a life (or a story) can be.

If you were intrigued by Orlando’s transformation across genders and centuries, you’ll be fascinated by The Left Hand of Darkness. Le Guin’s classic follows Genly Ai as he navigates the world of Gethen, where people are ambisexual and social norms are upended. The novel’s thoughtful, deeply humane exploration of gender and self makes it a spiritual sibling to Woolf’s work.

If you delighted in Orlando's witty, unconventional storytelling, you’ll revel in Pale Fire. Presented as a 999-line poem by a fictional poet, with wild, digressive commentary by an unreliable editor, Nabokov’s novel is a literary puzzle that toys with authorship, narrative voice, and the very nature of fiction—much like Woolf’s irreverent biography.

If Woolf’s lush, evocative prose in Orlando spoke to you, you’ll be moved by the lyrical beauty of The Color Purple. Walker’s novel, presented through letters, unspools Celie’s journey of self-discovery and resilience with language that sings, capturing both the pain and joy of transformation across time and circumstance.

If you loved following Orlando’s shifting identities across eras, you’ll find How to Be Both mesmerizing. Smith’s novel intertwines the stories of a Renaissance artist and a modern teenager, playing with time, perspective, and gender in inventive ways. The book’s structure even changes depending on the edition, offering a playful, profound exploration of how identity evolves.