On the ship to England, Orlando has to start learning to dress and act like an English woman. In the gypsy camp, women and men were generally treated the same, but now that Orlando is wearing the fancy dress of an English noblewoman, she is afforded privileges like an awning to sit under on the deck of the ship. However, she also starts to learn how important the appearance of modesty and chastity is to an English woman's reputation and worth. She experiences the dance of flirtation one must do when offered food: first refusing and then finally yielding. She then remembers that being too forward with such games, such as by throwing oneself off a boat to be rescued by a soldier, can get one called dirty names. She also considers that she wouldn't be able to save herself if she did fall in the water because of her long, heavy skirt. She remembers how she had the same opinion of women that other men did when she was a young man: "women must be obedient, chaste, scented, and exquisitely apparelled" (141). Realizing that these qualities do not come naturally or simply to women, she thinks of how she will have to spend a lot of energy working to meet the expectations of society.
As Orlando contemplates this, she accidentally kicks her foot in such a way that a sailor sees her calf, and the man almost falls off of the ship's mast. She becomes indignant at the fact that she must cover the best part of her body, her legs, and continues down a negative thought spiral, criticizing both men and women because she knows the weaknesses of both genders. As usual, she ruminates on these issues for days, only stopping briefly to go onshore in Italy. Eventually, she comes to the conclusion that it is better to be a woman. She reasons that even though women are denied education and agency, they are freed from manly desires for violence and power, and they can use that energy to pursue "contemplation, solitude, love" (144). Orlando now has to grapple with the fact that she, a woman, has loved women in the past. She still has feelings for them, particularly Sasha, and these feelings are deepened by understanding their experiences more as a woman herself.
As Orlando sits on the ship's deck lost in thought, the captain approaches her and points out that they are approaching England. Orlando is shocked by this, and she starts to question how she will integrate back into society when, as a woman, she cannot hold the land or titles she used to. She feels a confusing mix of negative emotions, thinking of Sasha and imagining having to marry a prince to have a stable life as a noblewoman. She reaches to her bosom and touches the manuscript of "The Oak Tree," which she keeps hidden inside her dress; as she thinks about poetry, her worries about gender subside. The captain points out the sights of London as they come into view; Orlando learns that a plague and a great fire occurred while she was away. Looking around her, Orlando vividly remembers the way London used to look, recalling the cobbled pavement, little houses, and the rushing water and icebergs on the day the Great Frost melted. Orlando notes that now the streets and shops look more clean and orderly; instead of taverns, people seem to gather to read and talk in coffee shops. As the ship sails past, the captain points out Addison, Dryden, and Pope sitting at a coffee shop together, which greatly interests Orlando.
Orlando arrives back in London and is immediately embroiled in an absurd legal case alleging that she can't hold property because, in short, it was "uncertain whether she was alive or dead, man or woman, Duke or nonentity" (151). Three sons of Rosina Pepita have claimed her property because their father was believed dead, but Orlando is allowed to return to her country home. There, she is greeted with extreme joy by the servants and even the animals. None of the servants is bothered by Orlando being a woman, and they even suggest that it is good Orlando is a woman because things around the house need mending and heirs need to be born. Orlando walks around the house looking at all of the beautiful rooms. In the chapel, she stops to examine a book that has a drop of Royal blood in it along with a lock of hair and a crumb of pastry; Orlando adds a flake of tobacco from her cheroot, a type of cigar she started smoking in Turkey. She sits in the chapel and thinks about God, religion, and poetry, coming to the conclusion that poets are extremely powerful and influential, perhaps even more so than religious leaders. She thinks back to how the gypsies hadn't been impressed with her lineage or possessions, and repeats to herself, "I am growing up...I am losing my illusions, perhaps to acquire new ones" (156). Moving to look out the window, she declares that England is better than Turkey.
Orlando begins working on "The Oak Tree" again. When she looks out the window onto a courtyard, she sees Archduchess Harriet, the woman who caused Orlando to move to Turkey and then followed her there. The Archduchess stares in Orlando's window, so Orlando invites the woman in. They compliment each other as ladies are expected to, but when Orlando goes to get wine out of a cupboard, she turns around to find the Archduchess transformed into a man. Orlando is shocked and confused. Archduchess Harriet, whom the biographer now switches to calling Archduke Harry, explains that he had been wearing a disguise because he realized long ago that he was attracted to Orlando but wouldn't be able to pursue him as a man. He falls to his knees, weeps, and again professes his desire to marry Orlando. The Archduke composes himself and promises to return the next day for Orlando's answer.
The Archduke returns the next day and every day after, and he and Orlando spend a lot of time together without Orlando agreeing to marry him. Orlando is very bored during these meetings, which mostly consist of the Archduke bragging and Orlando asking follow-up questions. Orlando teaches the Archduke a game called Fly Loo where they bet on which sugar cube a fly will land on, and this begins to take up a lot of their time. However, Orlando tires even of this game, so she starts cheating in more and more obvious ways so that the Archduke will become offended and leave her alone. The Archduke is so gullible that Orlando wins thousands of pounds in the process of cheating, but eventually the Archduke catches on and is properly angered. However, he calms down quickly and tells her that he forgives her because she is a woman. As a last resort to get the Archduke to leave her alone, Orlando takes a toad she had been hiding and puts it in the Archduke's shirt. Orlando laughs at the Archduke until he finally leaves.
Orlando is overjoyed to finally be alone again. However, she does lament that she lacks "Life and a lover" (164), a phrase with which she is so taken that she writes it down. Orlando dresses up in a fancy outfit, admires herself happily in the mirror, and then takes all of the clothing and jewelry off to reveal men's underwear underneath. She summons a carriage and leaves for London. During the carriage ride, the biographer takes a moment to talk about the interplay of gender and clothing, returning to the way Orlando was treated on the ship because of her dress and noting that women's clothing prevents women from protecting themselves. The biographer states that gendered clothing shapes society's view that gender is fixed; in fact, each person "vacillat[es] from one sex to the other...and often it is only the clothes that keep the male or female likeness" (168). The biographer goes on to say that Orlando has never been one fixed gender: though her sex changed from male to female, she has always been made up of elements that are traditionally male, like dressing quickly and understanding agriculture, as well as those traditionally female, like struggling with directions and feeling sympathy for animals.
Orlando moves into her city home and begins the search for life and a lover. After being in London for two days, Orlando finds love. While out on a walk alone, she is mobbed by common people, from whom the Archduke rescues her. The Archduke has not given up on marrying her, and even gives her a jewel in the shape of a toad as a lighthearted gift. Orlando begins to be invited to call upon by "the greatest ladies in the land" (170), which leads to her integration into London society as a whole. The biographer compares London society to "a mirage" (171) in that it seems incredibly fun and interesting while Orlando is there, but by the morning Orlando can not remember anything particularly interesting that occurred. Orlando takes many lovers during this time, but she still isn't sure if she has found life. The biographer mentions that, on a day in June of 1712, Orlando is fed up with society and humorously notes that society people talk about the same things her dog would talk about if he could talk: "I'm cold. I'm happy. I'm hungry. I've caught a mouse" (174). The fact that it is now 1712 means that almost 200 years have passed since Orlando was a young boy.
Orlando goes to bed thinking she will never go back into society again since the people and parties are vapid and worthless, but when she awakes she finds an invitation from the Countess of R-. Orlando immediately sends a messenger to reply that she'll go, knowing that the Countess of R- throws parties for only the most genius and witty socialites. Orlando attends the party and finds that, though everyone is reputed to be extremely witty, they actually chatter in the same boring way as everyone else. Orlando is invited back and continues to attend the Countess's gatherings. Finally, the third time Orlando attends, someone genuinely wise and witty speaks: Mr. Pope. What he says, which the biographer omits, causes everyone to go silent for twenty minutes and then leave. This seems not due to the statement's being rude, but rather being too much wit in a short period of time. As people leave the house, Orlando finds herself in the stairwell with Mr. Pope. She invites him to go home with her.
In the carriage on the way home, Orlando and Mr. Pope pass through areas of light and darkness because street's lamp-posts are quite spread out. Every time that they are in the darkness, Orlando thinks about how interesting Mr. Pope is and how lucky she is to be with him. When they are briefly in the light, Orlando suddenly sees the man as grotesque and feels ashamed for her veneration of fame and celebrity. As Orlando goes back and forth emotionally, she and Mr. Pope keep up light conversation. By the time that they get to Orlando's house, the sun has risen. Orlando realizes, with both disappointment and relief, that even geniuses are not genius all the time. Pope, Addison, and Swift, whom Orlando sees as the greatest minds of her day, all have their simple joys such as tea, a collection of colored glass, and gossip. Orlando begins to turn down opportunities to go out into society in favor of having these authors over to her home. The biographer includes passages from the works of Pope, Addison, and Swift, and explains how a reader can see a writer's soul from reading what they've written, meaning that authors are not so mysterious that critics and biographers are needed to explain them. By spending time with the authors, Orlando improves her writing, especially her ability to write in a naturalistic style, as if speaking.
One day Orlando is having tea with Mr. Pope and catches herself thinking, "How women in ages to come will envy me!" (188.) She realizes that she has once again been overly focused on celebrity and fame; Mr. Pope is actually lacking in many of the positive qualities one would want in an acquaintance, such as charity and tolerance. Furthermore, many poets have a very high opinion of themselves and low opinion of others, especially women. Thinking this, Orlando drops a sugar cube into Mr. Pope's tea in such a way that it splashes a little. Mr. Pope takes great offense to this, and he responds by saying something rude about women that he will eventually include in a work called Characters of Women. Mr. Pope leaves, and Orlando feels as if she had been slapped. She goes outside to take a walk and feels calmed by solitude and nature. She sits outside and thinks until evening.
When evening comes, Orlando goes into her room and dresses in an outfit she used to wear as a young man. She goes out into the city and passes as a man due to her clothing and her androgynous look. She meets a prostitute and goes back to her room, noticing that the girl puts on an act of timidity and stupidity to please her client. When Orlando reveals that she is a woman, the girl, Nell, immediately relaxes, laughing loudly and launching unprompted into the story of her life. Orlando enjoys hearing stories of a common person after being engaged in high society for so long, and in the following days Nell brings all of her friends to meet Orlando as well. The women tell Orlando about their negative experiences with men, who think that women do not have any actual desires, just "affectations" (193), and who think that women can't possibly enjoy the company of one another. The fact that Orlando enjoys spending time with these women debunks that notion, but the biographer wryly says that they will "leave it to the gentlemen to prove, as they are very fond of doing, that this is impossible" (194).
The biographer notes that this is another period of Orlando's life about which not much is known. She dresses as a woman and as a man whenever she pleased, often going back and forth multiple times in a day depending on her whims and engagements. She also takes a liking to standing outside a coffee house and watching the people talk inside, enjoying making up the things that they are saying based on their manner and gestures. On a particular evening, she watches three people—whom she calls Dr. Johnson, Mr. Boswell, and Mrs. Williams—for a long stretch; she describes it as being more engaging than any play she's seen. Then, one night, she comes home and looks out the window while she is undressing. As midnight approaches, she sees a giant cloud far off in the sky that grows and grows. As the clock sounds the last stroke of midnight, the cloud covers all of London. The biographer writes, "All was darkness; all was doubt; all was confusion. The Eighteenth century was over; the Nineteenth century had begun" (199).
As Orlando travels back to England, Woolf broaches the topic of homosexuality, which was hinted at in Orlando's youth. Like Woolf's introduction of gender transition through Orlando's lived experiences, the introduction to the topic of homosexuality is softened by readers knowing Orlando as a character and understanding the nuances of her sexual identity. Orlando reflects on Sasha, her female lover from when she was a young male, and finds that she is not disgusted by the thought of being sexually or romantically attracted to her, even now as a woman. In fact, Orlando finds that she is better able to empathize with Sasha since she now understands the challenges women face in life, particularly with the pressure to marry certain men for stability.
Many moments in Chapter IV point to Orlando's gender transformation giving her a rebirth or second youth. The fictional biographer explicitly notes that "It must be remembered that she was like a child entering into possession of a pleasurance or toy cupboard" (138) after Orlando considers throwing herself off the boat in the hope that some strapping sailor would save her from drowning. Later, Orlando's childishness is demonstrated in scenes with Archduke Harry, such as when she cheats at the game they've been playing and when she puts a toad in his clothing when he will not leave her alone. Not only do allusions to rebirth lend themselves to religious and psychoanalytical analyses and critiques of the novel, but Orlando's confusion over age, gender, sexuality, and status highlight the interplay of these matters in society.
Since the beginning of the novel, Orlando has derived pleasure from bending societal norms, particularly those that keep high- and low-class people physically apart. He not only enjoys high-class pleasures experienced in low-class places, such as when he brings Sasha to a village to make love in the snow, but he even likes having platonic and sexual relationships with low-class people themselves, like Sukey and Rosina Pepita. Orlando continues to flout the norms separating high- and low-class society while also experimenting with her gender presentation, alternating between male and female clothing and befriending prostitutes who begin to confide in her.
Clothing is highly important to Woolf's discussion of gender expectations and norms. Woolf writes early in Chapter IV, when Orlando contemplates jumping off the ship to be saved by a sailor, "Could I, however, leap overboard and swim in clothes like these? No! Therefore, I should have to trust to the protection of a blue-jacket. Do I object to that? Now do I?" (137.) Orlando's struggle with whether she likes the idea of needing to be saved is an early and crucial aspect of her questioning whether it is better to be a male or female, especially in English society. In this quote, Orlando focuses on the physical limitations imposed by female clothing. However, Orlando later solidifies a more negative perception of the limitations of women's behavior in less obvious ways. The biographer writes, "[Orlando] was becoming a little more modest, as women are, of her brains, and a little more vain, as women are, of her person...Vain trifles as they seem, clothes have, they say, more important offices than merely to keep us warm. They change our view of the world and the world's view of us" (166). It would seem more obvious that clothes change the world's view of someone, since one will look visually different with different clothes, but Woolf specifically highlights the notion that clothing and the norms that come with certain gender presentation feeds back into how someone acts and even how one thinks.
Besides gender commentary, a main function of Chapter IV is critique of English high society. Woolf parodies the norms of high society by describing how Orlando feels important, witty, and beautiful while attending lavish gatherings, but cannot remember anything of note the next day. Woolf also exposes the fact that famous people, especially authors, are fairly unremarkable most of the time. Orlando expects that the authors she meets, particularly Alexander Pope, will be witty and brilliant at all times, but she finds that they are actually witty only for one moment out of many hours and that they generally save their genius for their writing. Orlando also comes to realize that male authors in the 18th century did not actually respect female writers and socialites, no matter the outward shows of asking for criticism and company. It is likely that these critiques came directly from Woolf's experience as a female writer, even though she lived a century later: female writers in the 19th and 20th centuries still faced many authors and critics who questioned their value as writers and intellectuals.