Written as an elaborate joke biography, Orlando by Virginia Woolf contains critique on the social construction of feminine and masculine gender roles. As a modernist writer in the early twentieth century, Woolf examines sexuality and the rigid gender expectations of both women and men beginning during the renaissance and through the 1920's. Using an almost five hundred year old character, who experiences life both as a female and as a male, allows Woolf to explore the social evolution of gender from both perspectives.

Orlando begins life in the sixteenth century as an immensely successful male poet, aristocrat, and courtier of Queen Elizabeth I. As a typical aristocratic young man of the renaissance, he is looking for a wife while having a good time with all the girls along the way. He wears fine clothes that, although extravagant and feminine, were accepted and expected of men of his rank in the 1500's. However, while serving as an ambassador from England to Turkey, Orlando awakes from a deep, trancelike sleep to find himself a she instead of a he.

Regardless of her physical change, she is undaunted by her new sex because, "in every other aspect, Orlando remained precisely as he had been." Although physically a woman rather than a man, Orlando feels no differently than before, pointing to gender as socially constructed as opposed to biologically hardwired. In the beginning of her new identity, she also behaves no differently. While living away from society in the hills of Turkey as a gypsy, she does no experience any pressure to change her mannerisms from masculine to feminine. Gender and sexuality matter only within the confines of society.

However, as she boards a ship to England, Orlando finally realizes the strict gender roles imposed by society. While sitting on the deck of the vessel in the sun under a canopy the captain erected, she is rudely awoken to the social construction of gender by the reaction of a sailor to her bare ankle. She understands, also, that the building of shade from the sun for her was not done so out of consideration for her as a person but because she is female. Orlando even thinks about falling off the side of the ship just so a man can rescue her. Men rescued women from the water by necessity due to their massive quantities of skirts, which soon became waterlogged and heavy. Orlando debates with herself whether or not to put the trust of her rescue in a male sailor or not.

Completely clothing women in long, loose fitting shirts and modest, high cut blouses fulfilled another function of socially constructed gender roles. Chastity was held in higher regard for females than for males as Orlando quickly learns during her sea journey to England. As a man, Orlando freely kissed and laid down with many women without condescending chastisement from society. However, as a woman, Orlando comprehends a sexual double standard. From the reaction of the sailor, she realizes her affection for the opposite sex can no longer be openly displayed, let alone the exposed skin of her ankle, without public dishonor.

Upon returning to England, property ownership problems confront Orlando. He was presumed dead owing to his lengthy absence from civilization. His sons, if any, could therefore claim inheritance to his property. Conversely, Orlando is now a woman and as good as dead because women had no rights to holding property whatsoever. In either case, as a dead man or a live woman, Orlando had no legal rights to her estate. As another double standard, the latter speared a deeper wound. She found out just how inferior females were considered in a male-dominated society.

The eighteenth century dawns, and Orlando eventually begins wandering the streets at night dressed in masculine attire although still donning feminine dress during the day. Dressed as a man, she returns to her earlier masculine mannerisms. Throughout the day, Orlando figures out how to blend into eighteenth century English society while, at night, she is free to interact with society however she feels fit. Sexuality, she realizes, is merely how a person relates to the rest of the world.

Finally, wearing crinolines and petticoats, Orlando notices wedding bands on what seems like every hand of the newly emerged nineteenth century. Shrewd Victorian society repressed females more completely than any previous era. Respectable women were expected to marry as young as nineteen, produce child after child, and die faithful to their husbands. Orlando suffers in a time period of concealing limbs of furniture like concealing limbs of females but searches for a husband nonetheless. Shel, too, suffers in a stifling era of proper gentlemen. He is expected to find a suitable young wife and become the breadwinner of the family.

When Orlando reaches the twentieth century, she has matured and becomes tired of conforming to the gender expectations of each new age. She begins living as she desires and eventually realizes that she has actually been the same person her entire life. Orlando was merely conforming to society as expected by society, an important theme of the book.

Virginia Woolf examines the social construction of feminine and masculine gender roles in Orlando. With a character living in five centuries as both a woman and a man, Woolf explores the social evolution of gender from female and male perspectives. She examines sexuality and gender expectations beginning in the renaissance until the twentieth century with her unique modernist technique.