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.