Plot
In 1920s Copenhagen, portrait artist Gerda Wegener is attending an art show to support her husband, popular landscape artist and closeted trans woman Einar Wegener. Though Gerda is talented, she hasn't quite received the same success Einar has. The following day Gerda shows some of her work to a Museum curator but he's unfortunately unimpressed. When she returns home, she asks Einar to stand in for a female model, who is running late, to pose for a painting Gerda is working on. The experience of posing for Gerda's painting creates a string of events that brings out more of Einar's feminine identity, who is eventually named Lili.
The following day, Gerda mentions going to an artist ball, but when Einar refuses to go, she suggests that he go as someone else, namely Lili, and he agrees. They spend a few days preparing Einar, learning female mannerisms and donning him with make-up, new clothes and a woman's wig. All of which helps to bring out more of Lili's identity, but Gerda misinterprets it as a game. At the ball, Lili ends up spending the night talking with Henrik Sandahl. When Gerda looks for her, she sees the two of them kissing. When she confronts Einar about it the next morning, he says Henrik was kissing Lili.
Gerda shows the curator her new portraits of Lili and to her surprise, he agrees to show them. Lili goes to visit Henrik at his home and begins kissing him but when he calls her "Einar" she leaves devastated. When Gerda comes home, Lili tells her about Henrik and while Gerda sits at the table heartbroken, Lili turns back into Einar. She assures her that Einar has no romantic feelings for Henrik but Lili does, she also tells her that as a child Lili kissed a boy named Hans until Lili's father caught them. Afterwards, Gerda takes Lili to see Doctor Hexler who opts to treat Lili with radiation but after the procedure, Lili tells him he "hurt Lili". Hexler, convinced that Lili is insane, wants to have her admitted into an insane asylum on grounds of perversion.
Lili and Gerda relocate to Paris; Gerda's portraits of Lili in her feminine state attract serious attention from art dealers in a way that Gerda's previous portraits did not. Gerda tracks down art dealer Hans Axgil, Lili's childhood friend (whom Lili had kissed when they were young). Hans and Gerda's mutual attraction is a challenge as Gerda is navigating her changing relationship with Lili. Hans' long-time friendship with and affection for Lili causes him to support Lili and Gerda.
As Lili's gender identity becomes more challenging, and under the advice of Hans, Lili tries to seek help from psychologists, all of which are unhelpful with some believing her to be either homosexual or mentally ill. Eventually, at Ulla Poulsen's recommendation, Lili and Gerda meet Dr. Kurt Warnekros. Dr. Warnekros explains that he has met other transgender women. He proposes an innovative and controversial solution for Lili: male-to-female sex reassignment surgery.
He also mentions that this is the second time he has offered this surgery, but the first patient got too nervous and left before the surgery began.
This would entail a two-part procedure that involves first removing Lili's external genitalia and then, after a period of recovery, fashioning a vagina. He warns Lili and Gerda that it is a very dangerous operation which has never been attempted before, and Lili would be one of the first to undergo it. Lili immediately agrees and, soon after, travels to Germany without Gerda to begin the surgery.
Gerda stays behind for a while but ultimately decides she should be by Lili's side. After Gerda helps Lili heal, Lili begins working in a department store selling women's perfume. After enough time has passed, Lili decides it is time to go for the second surgery, much to Gerda's distress. Lili again leaves alone.
Gerda again shows up after the surgery is complete, but Lili is pale and weak but insists she be taken out to the garden again. Lili dies of complications from the second surgery with a heartbroken Gerda by her side. After her death, Gerda and Hans travel to a hilltop back in Denmark where Hans and Lili grew up, seeing all the landscapes that she painted, revealing that all of LiLi's paintings have always been connected to Lili.
The scarf that Lili had originally given Gerda, which had subsequently been given back and forth several times, is carried away in the wind, dancing.
