One of the most important themes in Orlando is the connection between fact and imagination. In Woolf's review of Harold Nicholson's Some People, she opened with this analogy: "if we think of truth as something of granite-like solidity and of personality as something of rainbow-like intangibility and reflect that the aim of biography is to weld these two into one seamless whole, we shall admit that the problem is a stiff one and that we need not wonder if biographers, for the most part failed to solve it." The metaphor of granite and rainbow emerges again in her own novel when she discusses Nature "who has played so many queer tricks upon us, making us so unequally of clay and diamonds, of rainbow and granite, and stuffed them into a case."
Woolf suggests that there is no realm of imagination separated from a realm of fact; "rainbow and granite" are stuffed into one case. Everything (internal and external, fact and imagination) are linked together by our memory, and we will grow to "understand" when we realize that neither memory nor history can be easily ordered and divided. Fact is a subjective quality, and the 'truth' emerges when we realize the interconnectedness and relativity of everything and everyone around us. It is such a unity of experience, not a triumph of "fact" that emerges victorious over time.
The determination of difference between the genders is a main theme in Orlando. Are men and women really different? If so, why? Orlando's sex change is a very important scene for determining the answers to these questions. As Orlando wakes up a woman, she looks at her body in a full-length mirror and composedly walks to her bath. She is not at all disconcerted by her change in gender because she feels no different than she did before. At first, she acts no differently, either. When she lives in the gypsy camp in the hills of Turkey, away from society and civilization, Orlando's sexuality seems to play no role in her life at all. But when she travels on board the English ship, in women's clothes, she immediately begins to feel the difference. The skirts that she is wearing, and the way that people react to her make her feel and act different. What Woolf is suggesting here is that gender roles are not biological, but societal. Gender is a concept imposed on people who live in society. When Orlando goes out into the night, a woman dressed as a man, she finds herself taking on traditional male mannerisms. The point is that when society allows the freedom of gender neutrality, people will be more free as individuals to act according to their nature and personality.
As Orlando is introduced to each new age and each new situation, he changes himself to fit the rules of those around him. In the sixteenth century, he wears fine clothes and serves as a courtier to his Queen; in the seventeenth century, he learns the Turkish language and adapts himself to exotic customs; in the eighteenth century, he figures out how to fit in with London society; and in the nineteenth century, he dons petticoats and finds a husband. Orlando knows he must change with each new adventure in order to survive and become accepted in the new age.
But such conformity becomes oppressive to Orlando. She grows tired of changing herself to fit those around her. Ultimately, when she reaches maturity in the twentieth century, she resists conforming, choosing instead to exist in her own internal world. She realizes that though she has matured, as people do, she has always been the same person all along. This theme of 'conforming to society' plays an important role in the novel. As Orlando grows to be an independent mind, she rejects the idea of conformity, choosing to remain however she chooses to be.
In every situation and adventure, Orlando carries with him the manuscript of his poem "the Oak Tree." When he begins the poem, he means it as a place to 'anchor his heart.' And indeed, the poem does become his anchor; the one thing which connects all his selves together. Poetry is not only an artistic release for Orlando; it functions in the work as a record of his maturation. As he grows, his writing style changes, from the simplistic metaphors of his teens, to the ornate language of his twenties, and finally to the simple lines of her thirties. Orlando guards the poem, as she guards her heart, utterly afraid of criticism and rejection. Ultimately, the poem ties the entire narrative together; it is a beginning (when a young boy sits under an oak tree) and an ending (when a middle-aged poem climbs to the tree to bury it). The poem is the record of Orlando's internal life.
Cross-dressing in Orlando occurs fairly frequently. Archduke Harry dresses as a woman but reveals himself to be a man in chapter four. Similarly, even after Orlando's actual sex change, he continues to switch between clothes of both genders. This motif functions in the novel to emphasize the similarities between men and women, despite the different clothes (and different roles) society would have them wear. Once she has experienced what it is like to be a woman, Orlando does not want to give this up, yet she longs for the freedom she had as a man. Here, Woolf suggests that perhaps society is too rigid with regard to the roles it forces men and women to play. Because they are so alike underneath their clothes, the genders should be allowed more freedom in their actions.
The clouds over London which move in at the end of chapter four mark the end of the eighteenth and beginning of the nineteenth century. They symbolize the suffocation and oppressiveness Orlando feels in the Victorian age. Because the sunlight can never come in through the clouds, the characters live with a literal chill in their bones and a figurative chill in their hearts. The clouds indicate unhappiness at the oppressive nature of Victorian rules and social conventions, especially for women like Orlando.
Orlando's large home is mentioned frequently throughout the novel. It appears as a static and safe element in a chaotic and changing world. The house symbolically has 365 bedrooms and fifty-two stairways (the number of days in a year, and the number of weeks in a year, respectively). It is significant that the house is marked by static, traditional measures of time, because the house provides regularity for Orlando, something she can always return to when she tires of her adventures in London or Turkey. Thus, it reminds the reader that while the narrative itself may skip over decades or centuries, Orlando continues to live within a framework. Time, as a concept constructed by her ancestors, encompasses Orlando and provides her a home.