Serious scholars have rarely taken Virginia Woolf’s novel Orlando, 90 years old this week, terribly seriously. It’s commonly described as a “romp” — lighthearted and fantastical, stretching more than three hundred years with an unaging hero who changes sexes midstream — a book to explain away rather than embrace. The explanation usually goes like this: From around 1925 until 1928, Woolf had a passionate affair with the aristocratic, bohemian, bisexual novelist Vita Sackville-West. In the words of Sackville-West’s son Nigel Nicolson, the novel is “the longest and most charming love-letter in literature,” and the character of Orlando a celebration of Sackville-West’s unconventional life.
But the story of Woolf’s gender-fluid and superhuman heroine is about much more than a single individual. As a work of political satire and feminist fantasy, Orlando laid the groundwork for today’s cultural landscape, in which the boundaries of both gender and literary genre are more porous than ever. Through a protagonist who, over the course of several centuries, takes multiple lovers and writes reams of poetry in every possible style, Woolf makes a joyful case for the transgression of all limits on desire, curiosity, and knowledge. Yet at the same time, Orlando constantly runs up against the limits of that freedom, exposing the persistent vise-grip of patriarchy even on a character blessed with the privileges of wealth, beauty, and close-to-eternal youth. Woolf invites us to imagine what it would feel like to escape, and yet, over and over again, reminds us that we are trapped. When we talk today about the tantalizing potential of a gender-agnostic society, of a world in which masculine and feminine traits are recognized for the performances that they are, or when we explore such possibilities in fiction and fantasy, we do so in Orlando’s shadow.
During the week of the novel’s release, Woolf gave the first of two talks at Cambridge that became A Room of One’s Own, which was published in 1929 and is now read as a classic of feminist polemic. Ahead of the release of that book, Woolf suspected it might be dismissed, along with Orlando, for having too much “charm” and “sprightliness.” She worried that her illustrious male friends would give it only “evasive, jocular” criticism, refusing to engage with its ideas. About Orlando, she wrote defensively, “I want fun. I want fantasy,” perhaps to preempt dismissive half-praise. Even the author seemed unwilling to acknowledge the political edge in her playful skewering of gender roles, her creation of a protagonist who is bound by neither of the two forces that define us as human: sex and death.
Both books express the same frustration, roaring to the surface again nearly a century on — the specific impossibility of living a full human life once society, in one form or another, has labeled you a woman. In both volumes, Woolf explores and clarifies the insidious enforcement of masculine power: through money, through status, through freedom of dress and movement, through the right to speak in public and be heard and believed. Woolf points out over and over again that what makes men men is their power, and what makes women women is their lack of it: financially, culturally, and physically.
In A Room of One’s Own, Woolf used the imaginary figure of Shakespeare’s forgotten sister to illustrate the historic limitations on women’s creativity, and to suggest that it was only now, in her own moment, that women writers could begin to achieve recognition. Orlando follows the same timeline, from the 16th century to Woolf’s exact time and place, England in October 1928. When Orlando is not much more than a boy, he is presented to Queen Elizabeth; the elderly monarch takes a shine to him, and as a consequence, “Lands were given him, houses assigned him.” While Elizabeth’s infatuation with Orlando is feminine, her power is not. In a speech to rouse the troops against the invading Spanish Armada, the Virgin Queen famously declared, “I may have the body but of a weak and female woman, but I have the heart and stomach of a king.” Her favor endows Orlando, as a man, with property and power.
Orlando is presented at court and pursued by a number of potential wives; instead, he falls in love with a gender-ambiguous Russian princess named Sasha, who breaks his heart. He is appointed ambassador to Constantinople, elevated to the status of duke, and then, after a days-long sleep, he awakens one morning as a woman. For a brief interlude after Orlando’s male-to-female transformation (or transition), Woolf raises the possibility of not being bound by sex at all, and tries speaking of Orlando with “they” pronouns, as a person containing both male and female selves: “The change of sex, though it altered their future, did nothing whatever to alter their identity. Their faces remained, as their portraits prove, practically the same.” After these two sentences, however, the narrator-biographer bows to convention and begins to call Orlando “she.” But the glimpse of a nonbinary pronoun is tantalizing. It would take decades for the singular, gender-evasive “they” to take hold in the lexicon (Merriam-Webster dates the first use to the 1950s) and for the culture to catch up to Orlando’s casual claim that “in every human being a vacillation from one sex to the other takes place.”
The character’s transition is more gradual than the shift to the feminine pronoun suggests. At first, Orlando adopts unisex Turkish trousers, and it is not until she feels “the coil of skirts about her legs” and the changed attitudes of observing men that she starts to grasp the consequences of her new identity. Her once-secure grasp on her estates and her noble position are suddenly subject to lawsuits that drag on for hundreds of years. The female Orlando’s fortune is reduced to the strands of pearls and emeralds wrapped around her neck, portable and removable, instead of being connected, body and soul, to her land, where she used to lie and feel the roots of an oak tree like a “spine” beneath her. The rest of the novel is about the financial and emotional consequences of being a woman in a society created and run by men, for men.
Back in London, at the end of the 18th century, Orlando spends her time attempting to glean the wisdom of the great male wits of the age, Pope, Addison, and Swift, but her sex makes it impossible to speak freely with them. She can hardly get a word in, and is ignored and patronized when she does. Frustrated, Orlando dons her old masculine clothing, takes to the streets, and picks up a prostitute, with whom she can finally have a frank conversation, woman to woman.
In Sally Potter’s 1993 film adaptation, starring the appropriately ageless and shape-shifting Tilda Swinton, the elaborate costumes make it clear that our ideas of what makes a certain appearance “masculine” or “feminine” are constantly changing and perennially absurd. From the ballooning breeches of the Elizabethans, through the Enlightenment’s monstrous wigs, and on to the crinolines of the Victorians, clothes are designed to highlight or conceal the body, to enable or restrict movement, and to declare both sex and social status. But clothing by itself cannot make men or women. Only power can do that.
Woolf describes the arrival of the Victorian era as the encroachment of damp on the landscape, buildings, furniture, bodies, and souls of the English: “The sexes drew further and further apart. No open conversation was tolerated … the life of the average woman was a succession of childbirths.” Even Orlando — previously bent on pursuing “life!” and “a lover!” — is suddenly made physically aware, by a vibration on the naked third finger of her left hand, of her lack of a husband. Marriage and monogamy are the unavoidable spirit of the age; meanwhile, the courts have finally determined that Orlando is alive and a woman, so that the ownership of her estates now depends on the production of a male heir. A domestic, dependent Orlando would be no fun, however, so Woolf gives her a husband who stays just long enough to get that ring on her finger before setting sail for Cape Horn.
The narrator purports to be Orlando’s biographer, and the novel cheekily adopts the genre’s conventions, including portraits and a reference index, which thoroughly confused early booksellers who weren’t sure what the book was. Woolf’s father, Leslie Stephen, was the first editor of the Dictionary of National Biography, a classic Victorian-era project to categorize the “great men” of the national past, and she had a lifelong fascination with biography.
In 1928, the stalwart genre rarely made space for any woman, let alone one as rebellious as Vita Sackville-West. (And even in our enlightened times, “straight” biographies of female subjects are in a significant minority.) Despite Orlando’s broad interest in the way gender shapes lives throughout history, there’s truth in what Nigel Nicolson said, with a twist: It is not a love letter but a biography of a lover, disguised as the fictional biography of an even less conventional subject.
Born at Knole, her family’s ancestral estate in Kent, Vita was the only child of cousins Victoria Sackville-West and the third Baron Sackville, and grew up knowing that because of her sex she would never — could never — inherit her own home. The estate passed to a male cousin; she did not marry him, but instead chose Harold Nicolson, a diplomat and writer, who had roughly as many homosexual affairs as his wife did. Before Virginia, Vita’s most serious lover was Violet Keppel, whom she often went out with dressed as a man, passing herself off as Violet’s husband.
In Constantinople, where Orlando’s sex change takes place, Sackville-West lived the life of a diplomat’s wife and wrote the poems that would launch a long literary career. Woolf could be sniffy about Sackville-West’s dashed-off novels, but in the 1920s, her fame as a writer far eclipsed Woolf’s. Sackville-West’s cross-dressing; the “gypsy” blood inherited from her mother’s mother; her prolific, uneven writing — all would come to define the character of Orlando. Yet, to Woolf’s consternation, Sackville-West never fought for her claim to Knole, nor resisted the structures of power that so easily cast her aside.
Woolf wrote afterward that she began to write Orlando as a joke. She doesn’t get enough credit for her sense of humor in general, but it is clearly on display in this, her most playful book. It’s still daring for literature, especially the kind we call classics, to be as much fun as this. If published today, Orlando might have been misshelved not as biography but as fantasy or science fiction — genres in which women writers in recent years have increasingly found the space to challenge the straight-white-male strictures of both realist fiction and reality itself. Orlando’s blend of social critique and bold fantasy echoes in the postwar fiction of Ursula Le Guin and Angela Carter, and more recently in the fairy-tale retellings of Helen Oyeyemi and Daniel Mallory Ortberg — as well as in novels like Melissa Broder’s The Pisces, in which a graduate student writing on Sappho falls in love with a merman.
Woolf grasped intuitively that narrative daring and insouciance could be driven to political ends, that lightness of heart did not mean an absence of conviction, but she remained unconvinced that her contemporaries would get it. In that sense, Orlando feels like an artifact from and for the future, a character who refuses to be bound by conventions, and who invites us to consider the possibility that all of our certainties are in fact contingencies. Although buffeted by the changing expectations of each succeeding “age,” Orlando nevertheless asserts herself over and over again, as a fully human being.