Orlando (Tilda Swinton) is an Elizabethan nobleman who perfectly fits the effeminate, sensitive male fashion of the day. Queen Elizabeth (Quentin Crisp) is struck by Orlando's androgynous beauty and commands him to never age to keep his family's land holdings. Somehow Orlando does just that for 400 years. He is dreamy and naive in the matters of relationships, espousing poetry and looking for meaning in life's petty happenings. Orlando accepts a diplomatic post in India after his heart is broken by a beautiful Russian and he becomes increasingly disillusioned by the constraints of the male gender. No one seems to notice he has lived 200 years and when Orlando wakes up as a woman and eventually returns to England, no one in the polite British society deigns to notice as well. Orlando lives out the next 200 years as woman, finding that both sexes have their constraints. She rejects unwanted marriage offers that would enable her to keep her estate as a woman and refuses to accompany the swashbuckling Shelmardine (Billy Zane) to America. The life of Orlando takes the viewer on a journey that shows both sides of the coin of the male/female existence.