Written as a witty and parodic biography of its protagonist, Orlando, Orlando charts the life and times of its central character from a masculine identity within an Elizabethan Court to a feminine identity in 1928.

This novel provides an analysis of the historically constituted subject, and a critique of gender essentialism while it also explores the important issue of gender and creativity. Subjectivity is presented by Woolf as multifaceted and as a multiplicity of conflicting elements. Orlando further reiterates what Woolf sees as the key problematic of sexual politics: the tension between androgyny and the articulation of sexual difference.

Woolf observes that after her male protagonist becomes a woman, "in every other respect, she remained precisely as he had been" implying that sexually defined selves or roles are merely costumes we wear and that they are readily interchangeable. Further, "it was a change in Orlando herself that...