[In the excerpt below, Woodbridge contends that transvestite disguise in Shakespeare's plays tends to reinforce, rather than undermine, traditionally perceived differences between the sexes.]

During the 1590s, Shakespeare frequently used transvestite disguise in his plots; other dramatists used it occasionally. It is true that, as Juliet Dusinberre says, [in Shakespeare and the Nature of Women, 1975], "disguise invites the dramatist to explore masculinity and femininity"; it is probable, however, that the feminism resulting from such explorations has been over-estimated. Writing that "Shakespeare's feminism is not optional, to be taken or left according to the critic's taste," Dusinberre notes that "disguise freed the dramatist to explore … the nature of women untrammelled by the custom of femininity." But most dramatists … regarded femininity as a matter of nature rather than custom; and as such it could never be sloughed off with clothes. Granted, masculine disguise gives heroines certain unwonted freedoms: sometimes a woman travelling alone adopts male clothing to discourage rape ("Beauty provoketh thieves sooner than gold," As You Like It, I.iii.l12); sometimes, like Portia in The Merchant of Venice, she must adopt male dress to practice a profession barred to women; sometimes she dresses as a man to effect a daring escape or for the sheer love of adventure. The dramatists saw clearly enough that women qua women could not easily travel alone, plead a case at law, have adventures. It is at least possible, given the spirit and intelligence with which they endowed their heroines, that they saw something unfair about these restrictions. But the dramatists insistently remind us that such behavior, however necessitated by emergency circumstances, is unnatural. Julia, who dons a page's costume to "prevent / The loose encounters of lascivious men," worries about her reputation: "But tell me, wench, how will the world repute me / For undertaking so unstaid a journey? / I fear me, it will make me scandalized" (Two Gentlemen of Verona, II.vii.40-41, 59-61). She reproaches her lover for having forced her to such a shift: "O Proteus, let this habit make thee blush! / Be thou ashamed that I have took upon me / Such an immodest raiment" (V.iv.104-106). Jessica too sees her boy's disguise as shameful: "I am glad 'tis night, you do not look on me, / For I am much ashamed of my exchange. / … Cupid himself would blush / To see me thus transformed to a boy. / … What, must I hold a candle to my shames?" (Merchant of Venice, II.vi.34-41). Viola's "masculine usurped attire" represents behavior, according to Orsino, "much against the mettle of your sex. / So far beneath your soft and tender breeding" (Twelfth Night, V.i.257, 330-331). The idea that wearing male clothing implies a change in her feminine nature shocks Rosalind: "Dost thou think though I am caparisoned like a man, I have a doublet and hose in my disposition?" (As You Like It, III.ii.204-206). Upon hearing that Orlando is near, she is as perturbed as Jessica before Lorenzo: "Orlando? … Alas the day! What shall I do with my doublet and hose?" (III.ii.229-231).

Dusinberre's most attractive theory about male disguise is that "the masculine woman and the woman in disguise are both disruptive socially because they go behind the scenes and find that manhood describes not the man inside the clothes, but the world's reaction to his breeches.… A woman in disguise smokes out the male world, perceiving masculinity as a form of acting." This may well have been true for the "masculine woman," by which Dusinberre means the man-clothed woman of Jacobean times; but unfortunately it does not ring true for Shakespeare's transvestite heroines. When Rosalind dons curtle-axe and boar-spear to declare, "In my heart / Lie there what hidden woman's fear there will, / We'll have a swashing and a martial outside, / As many other mannish cowards have / That do outface it with their semblances" (As You Like It, I.iii. 120-124), and when Portia takes up a dagger to disguise herself "like a fine bragging youth" (Merchant of Venice, III.iv.69), what they expose as "a form of acting" is not masculinity but the feigned masculinity of the braggadocio. This is to say nothing: the coward had hidden behind the braggadocio role in literature from classical antiquity to Falstaff. To advance from this convention to the perception that the "true" masculinity of an Orlando and the "true" femininity of a Rosalind are merely artificial roles is a large step—a step Shakespeare did not take. Nothing in Shakespeare suggests that but for a little artificial social conditioning, an Orlando would faint at the sight of blood, or a Rosalind challenge Charles the wrestler. Shakespeare's transvestite heroines do not approach any nearer to true manhood than do the fraudulent "mannish cowards." In the confrontation between Sir Andrew Aguecheek and Viola, we are invited to laugh with mild contempt at the male coward and with affectionate indulgence at the female coward: cowardice violates his nature but is a natural expression of hers. Transvestite disguise in Shakespeare does not blur the distinction between the sexes but heightens it: case after case demonstrates that not even masculine attire can hide a woman's natural squeamishness and timidity. King Lear must disrobe to find the essential nature of a human being; a woman's essential nature, Shakespeare insists, shines through any kind of clothes. When Shakespeare's romantic heroines play at being men, Shakespeare invites us to smile at their trepidations and their posturings, with the affection of a parent watching his child play at being grownup. His obvious good will, and the central roles he assigns these heroines, keeps the condenscension from being offensive. But neither is it feminist. As Paula S. Berggren notes [in The Woman's Part: Feminist Criticism of Shakespeare, edited by Carolyn Ruth Swift Lenz, Gayle Greene, and Carol Thomas Neely, 1983], "While the wearing of pants allows expression of a talent otherwise dampened by convention, it does not, in Shakespeare, lead to a direct challenge of the masculine order." Shakespeare's transvestite heroines are "content to reassume their womanly duties."

All but one of Shakespeare's transvestite heroines belong to the 1590s, when female transvestism was out of fashion on the London streets. After the fashion was revived in early Jacobean London, Shakespeare largely abandoned the device. His sole remaining female transvestite, Imogen in Cymbeline, is ill at ease in her masculine weeds: as Dusinberre points out, "Rosalind and Portia thrive on the masculine life where Imogen wilts beneath it." In All's Well, Shakespeare seems to avoid the device deliberately; Helena travels alone to the court and the wars without adopting male disguise. There are many possible explanations for Shakespeare's abandoning such a cherished plot device; among them is that he recoiled from the sight of real-life women in breeches.

Shakespeare's plays contemporary with the revival of masculine attire among London women (Macbeth, 1606, Antony and Cleopatra, 1607, Coriolanus, 1608) take a persistent interest in women who violate their "natural" sex roles. Shakespeare is not without sympathy, in these plays, for the frustrations of a woman who must live a vicarious life of action through a man who has more freedom to act than she does. But the yearnings of such women for masculinity must have disturbed him: none of his breeches-envying tragic heroines of this period is treated with unqualified approval.

Lady Macbeth's attempt to unsex herself, so as to put on the power and ruthlessness she attributes to men, is foreshadowed by the hermaphroditic witches—bearded women. Macbeth sees her driving ambition as masculine: "Bring forth men-children only, / For thy undaunted mettle should compose / Nothing but males" (I.vii.72-74). But she goads a man into action rather than acting herself. Volumnia's life of action is accomplished vicariously through her son, Coriolanus, whom she imagines fighting, bleeding; when he returns from battle she counts his fresh wounds to keep her tally up to date. "Thou art my warrior," she reminds him; "I holp to frame thee" (V. iii. 63-64). When she is accused of being mannish, she considers it a compliment: "Aye, fool, is that a shame? … / Was not a man my father?" (IV.ii.17-18). Cleopatra, too, is frustrated by the narrow sphere of action allotted to her sex. She imagines Antony riding his horse, commanding his troops. She reports having tried on his sword. Her outburst to Antony, "I would I had thy inches" (I.iii.39), is telling; given her propensity for suggestive remarks, it is unlikely to refer solely to his height. Her one foray into battle is prefaced by a cool verbal sex change: she says she will "appear there for a man" (III.vii.19). The exercise is disastrous. But then Cleopatra has had little experience being a man.

Both the fact that in the 1590s Shakespeare took pains to assert through his transvestite heroines that despite appearances to the contrary, women have a fixed and immutable nature that will declare itself eventually, and the fact that during the early Jacobean years he interested himself in women who try to step out of that feminine nature, showing how such attempts invariably eventuate in failure, death, and/or authorial disapproval, suggest that Shakespeare had caught a whiff of the winds of sexual change blowing in his own culture. The idea that sex roles might alter was apparently an aroma which seared his nostrils.