Orlando is Virginia Woolf’s testimony to the woman she was in love with, Vita Sackville-West. The “biography’s” hero(ine) flits between genders, travels through the centuries from the Elizabethan era to the modern day, and delights the reader with his/her many adventures. This playful mock biography is Virginia Woolf at her most light-hearted and yet Orlando still conveys some important messages about Woolf’s perception of gender roles and sexuality, and the significance of the society an individual must inhabit and the rules s/he is subject to. Woolf suggests that gender is as fluid as the clothes one wears and that being born male or female does not necessarily mean that your gender matches. When Orlando is a man and seduces the Russian princess, Sasha, he is free to reject the woman he was engaged to in order to pursue his new love interest. However, in the Victorian era, when Orlando is a woman, she is stripped of her aristocratic right to inherit her family’s estate because she is a woman and is trapped within the large, cumbersome crinolines that were the fashion of the time. The symbolic nature of clothes is apparent throughout the text as Orlando is liberated and subjugated in turn. Woolf’s witty and exciting biography, perhaps the most inventive love letter ever written, escaped the notice of the obscenity activists at the time despite its lesbian purpose and content. The subtle inclusion of love between women stands in contrast to the less skilful attempt made by Radclyffe Hall in The Well of Loneliness. While Hall’s novel was successfully banned, Woolf’s lyrical and mischievous work was published and enjoyed. The text even includes photographs of Vita which serve to interweave fact with fiction. Orlando truly is a masterpiece as it tackles the difficult and contentious subject matter of gender roles with humour, playfulness, and subtlety.