Orlando, to look at, was cut out precisely for some such career. The red of the cheeks was covered with peach down; the down on the lips was only a little thicker than the down on the cheeks. The lips themselves were short and slightly drawn back over teeth of an exquisite and almond whiteness. Nothing disturbed the arrowy nose in its short, tense flight; the hair was dark, the ears small, and fitted closely to the head. (1.2)
The language first used to describe Orlando isn’t particularly masculine.
'Lord,' she thought, when she had recovered from her start, stretching herself out at length under her awning, 'this is a pleasant, lazy way of life, to be sure. But,' she thought, giving her legs a kick, 'these skirts are plaguey things to have about one's heels. Yet the stuff (flowered paduasoy) is the loveliest in the world. Never have I seen my own skin (here she laid her hand on her knee) look to such advantage as now. 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?' she wondered, here encountering the first knot in the smooth skein of her argument. (4.2)
Being a woman comes with certain pleasures and penalties. Orlando is working them out for the first time since she wasn’t raised as a woman.
She remembered how, as a young man, she had insisted that women must be obedient, chaste, scented, and exquisitely apparelled. 'Now I shall have to pay in my own person for those desires,' she reflected; 'for women are not (judging by my own short experience of the sex) obedient, chaste, scented, and exquisitely apparelled by nature. They can only attain these graces, without which they may enjoy none of the delights of life, by the most tedious discipline. There's the hairdressing,' she thought, 'that alone will take an hour of my morning, there's looking in the looking-glass, another hour; there's staying and lacing; there's washing and powdering; there's changing from silk to lace and from lace to paduasoy; there's being chaste year in year out...' (4.7)
Aha! The tables have been turned on Orlando. Here she realizes how male opinions, wants, and desires influence female actions. Orlando sounds particularly angry about not getting to have sex now that she's a woman.
The comforts of ignorance seemed utterly denied her. She was a feather blown on the gale. Thus it is no great wonder, as she pitted one sex against the other, and found each alternately full of the most deplorable infirmities, and was not sure to which she belonged--it was no great wonder that she was about to cry out that she would return to Turkey and become a gipsy again… (4.8)
Knowing what it’s like to be both sexes, Orlando becomes confused and longs for her androgynous life among the gipsies.
'Better is it', she thought, 'to be clothed with poverty and ignorance, which are the dark garments of the female sex; better to leave the rule and discipline of the world to others; better be quit of martial ambition, the love of power, and all the other manly desires if so one can more fully enjoy the most exalted raptures known to the humane spirit, which are', she said aloud, as her habit was when deeply moved, 'contemplation, solitude, love.' (4.11)
In one thought, Orlando delineates how feminine compliance to male domination comes with certain rewards. Does she really believe this?
And as all Orlando's loves had been women, now, through the culpable laggardry of the human frame to adapt itself to convention, though she herself was a woman, it was still a woman she loved; and if the consciousness of being of the same sex had any effect at all, it was to quicken and deepen those feelings which she had had as a man. For now a thousand hints and mysteries became plain to her that were then dark. Now, the obscurity, which divides the sexes and lets linger innumerable impurities in its gloom, was removed, and if there is anything in what the poet says about truth and beauty, this affection gained in beauty what it lost in falsity. At last, she cried, she knew Sasha as she was, and in the ardour of this discovery, and in the pursuit of all those treasures which were now revealed, she was so rapt and enchanted that it was as if a cannon ball had exploded at her ear…(4.11)
Being a woman now gives Orlando insights into the feminine character. Thinking over her relationship with Sasha, she comes to new conclusions about Sasha’s motivations and character. What do you think she learned about Sasha? Also, was it necessary for Orlando to become a woman in order to clearly see Sasha’s character?
Orlando sipped the wine and the Archduke knelt and kissed her hand.
In short, they acted the parts of man and woman for ten minutes with great vigour and then fell into natural discourse. (4.33 – 4.34)
Being a "man" and being a "woman" can be "acted." Their genuine selves are different.
The distraction of sex, which hers was, and what it meant, subsided; she thought now only of the glory of poetry, and the great lines of Marlowe, Shakespeare, Ben Jonson, Milton began booming and reverberating, as if a golden clapper beat against a golden bell in the cathedral tower which was her mind. (4.16)
A love for literature is not gendered. In fact, Orlando can think about literature without having to give her new sex any consideration.
Thus, there is much to support the view that it is clothes that wear us and not we them; we may make them take the mould of arm or breast, but they mould our hearts, our brains, our tongues to their liking. (4.48)
According to this passage, it’s not genitalia that make us a man or a woman, it’s the clothes we wear. Orlando is treated differently and behaves differently when she is wearing female clothing rather than male clothing. Furthermore, the importance of clothes is a direct result of society. Orlando never really felt like a woman among the gipsies because they wore unisex clothing.
The difference between the sexes is, happily, one of great profundity. Clothes are but a symbol of something hid deep beneath. It was a change in Orlando herself that dictated her choice of a woman's dress and of a woman's sex. And perhaps in this she was only expressing rather more openly than usual--openness indeed was the soul of her nature--something that happens to most people without being thus plainly expressed. For here again, we come to a dilemma. Different though the sexes are, they intermix. In every human being a vacillation from one sex to the other takes place, and often it is only the clothes that keep the male or female likeness, while underneath the sex is the very opposite of what it is above. (4.48 – 4.49)
This is arguably one of the most important passages of the novel. Woolf says that we all have male and female qualities. Only the gender of clothing remains absolute – the gender of human beings is actually quite plastic. Although Orlando could have stuck to male clothing, (s)he had shifted to more female qualities and sought to express that in her choice of clothes.
For it was this mixture in her of man and woman, one being uppermost and then the other, that often gave her conduct an unexpected turn. The curious of her own sex would argue, for example, if Orlando was a woman, how did she never take more than ten minutes to dress? […] And then they would say, still, she has none of the formality of a man, or a man's love of power. She is excessively tender-hearted. She could not endure to see a donkey beaten or a kitten drowned. Yet again, they noted, she detested household matters, was up at dawn and out among the fields in summer before the sun had risen. […] Though bold and active as a man, it was remarked that the sight of another in danger brought on the most womanly palpitations. She would burst into tears on slight provocation. […] Whether, then, Orlando was most man or woman, it is difficult to say and cannot now be decided. (4.50)
Although Woolf portrays Orlando as having an androgynous mix, she still assigns various qualities to either gender.
As that is not a question that can engage the attention of a sensible man, let us, who enjoy the immunity of all biographers and historians from any sex whatever, pass it over, and merely state that Orlando professed great enjoyment in the society of her own sex, and leave it to the gentlemen to prove, as they are very fond of doing, that this is impossible. (4.90)
So the biographer is asexual. Would it change anything if the biographer did have a gender? If so, what?
Fame! (She laughed.) Fame! Seven editions. A prize. Photographs in the evening papers (here she alluded to the 'Oak Tree' and 'The Burdett Coutts' Memorial Prize which she had won; and we must snatch space to remark how discomposing it is for her biographer that this culmination to which the whole book moved, this peroration with which the book was to end, should be dashed from us on a laugh casually like this; but the truth is that when we write of a woman, everything is out of place--culminations and perorations; the accent never falls where it does with a man). Fame! she repeated. A poet--a charlatan; both every morning as regularly as the post comes in. To dine, to meet; to meet, to dine; fame--fame! (6.74)
This suggests that had Orlando been a man at this point, the biography would have ended. Since men seek glory and ambition, winning awards for poetry should signal the final end and triumph of the novel.