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On June 12, 1901, prominent New York architect Stanford White takes his ailing wife Elizabeth to lunch before she leaves for a long vacation.  Their lunch is interrupted by Harry Kendall Thaw, an arrogant, wealthy young man from Pittsburgh who deeply resents White’s higher placement in New York’s rigid social structure.  White reprimands Harry for his childish behavior, and after Harry leaves, he and Elizabeth are greeted by publisher Robert Collier, who shows them the latest issue of his magazine.  Elizabeth admires the cover illustration, drawn by famed artist Charles Dana Gibson, of a lovely young woman whose long hair forms a question mark.

Later, in a music hall, Evelyn Nesbit, the woman in the illustration, visits her mother, who works there as a seamstress.  The overprotective Mrs. Nesbit tells Eveyln that she will be unable to chaperone her session with Gibson that day, but Eveyln’s disappointment is tempered when the stage manager asks her to become one of the chorus girls in the famed "Floradora" musical revue.  Sometime later, White is visited by a friend, Gwen Arden, who asks him to arrange a meeting for her with Collier.  When White spots Evelyn in Gwen’s carriage, he is struck by her beauty and agrees to a luncheon, provided that Gwen brings Evelyn.

Soon after, Gwen, Evelyn and the other girls are invited by Harry to his birthday party the following day.  At the party, Harry is infuriated when he learns that Gwen and Evelyn are not in attendance because they are with White.  Meanwhile, the women have gone to White’s private apartment, and there, the naïve Evelyn is overwhelmed by the luxurious surroundings, especially an extravagant arboretum containing a red velvet swing suspended from the ceiling.  Sitting in the swing, Evelyn innocently asks White to kiss her, and the couple is surprised when what they intended to be a platonic kiss becomes passionate.  Realizing that he could easily fall in love with Evelyn, White tells Gwen never to bring her to see him again, although he does pay to have her chipped tooth repaired.  Mrs. Nesbit reprimands her daughter for seeing the much older, married White, but Evelyn protests that he is the greatest man she has ever met.  Hoping to see White, Evelyn goes to his apartment but he warns her that the attraction between them is too strong for them to meet again.

Later, Evelyn is at the beach, posing for Gibson, when Harry races by in his carriage to impress her.  Soon after, White arrives at his club for a stag party and is upset to learn that Evelyn has been hired to jump out of an oversized pie.  White sternly tells her that he will be nothing more to her than a “Dutch uncle,” and that she must behave more decorously.  White’s honorable intentions fail, however, as they spend more time together and fall in love.  Later, Evelyn and Mrs. Nesbit, who knew Harry as child, are shopping when Harry attempts to buy Evelyn a fur coat.  Evelyn again rejects Harry’s overtures, but Harry pleads with Mrs. Nesbit to support his suit.  Soon after, Evelyn, who has become a success on the stage and is being pursued by many men, eagerly awaits a visit from White.  When he arrives backstage, however, he is met by Mrs. Nesbit, who criticizes him for his infidelity.  Ashamed, White tells Evelyn that they must end their affair, and that she must go away to boarding school.  Although she is deeply hurt, Evelyn agrees to go, but after a few weeks, has an emotional breakdown because of her longing for White.

Evelyn is visited by Harry, who suggests to Mrs. Nesbit that she needs a complete rest and offers to escort them to Europe.  Mrs. Nesbit agrees, but when White learns of the plans, he attempts to intervene.  Before he can complete his arrangements, White learns that Elizabeth is coming home, and so instead sends a letter of credit to Evelyn so that she will be financially secure in case Harry abandons her.  While on vacation, Harry repeatedly proposes to Evelyn, but when she admits that she was White’s mistress, he slaps her.  Harry’s remorse over his outburst makes Evelyn see him in a new light and she agrees to marry him.  White is glum upon hearing of the impending marriage, and when he learns that Harry is insisting that Evelyn’s repaired tooth be restored to its former chipped state, he arranges to meet Evelyn at the dentist’s office.  There, White begs her not to marry the mentally unstable Harry, but Evelyn maintains that she cannot spend the rest of her life as White’s mistress, even though she still loves him.

During Evelyn and Harry’s honeymoon, Harry’s persistent questioning of her relationship with White drives Evelyn to the brink of another collapse, and she wearily allows Harry to think that White drugged and raped her.  Harry refuses to believe Evelyn’s insistence that her affair with White is over, and one night, when they visit the nightclub on the roof of Madison Square Garden and Harry spots White, he assumes that White is following Evelyn.  Overcome by jealousy, Harry shoots and kills White, then yells that he committed the crime because White “ruined” his wife.

After Harry’s arrest, the District Attorney announces that he will seek the death penalty if Harry is convicted, and Harry’s overbearing mother hires lawyer William Travers Jerome to defend him.  Mrs. Thaw and Delphin Dalmas, Harry’s sister, pressure Evelyn to testify on Harry’s behalf, and to besmirch White’s reputation.  Gibson begs Evelyn not to testify, and despite her reluctance to refute her love for White, the fear that Harry will be put to death prompts Evelyn to testify on his behalf.  The District Attorney viciously attacks Evelyn, bringing up such facts as White’s letter of credit to paint her as a gold-digger.  Despite the damage to her reputation, Evelyn’s testimony sways the jury, which returns a verdict of not guilty by reason of insanity.

Later, when Harry is being transferred to a mental institution, he harshly rejects Evelyn’s offer to move near him.  As Evelyn leaves the jail, she is accosted by reporters, after which a seemingly friendly stranger rescues her.  The man then reveals that his name is Hunchbacher and that he runs a vaudeville theater in Atlantic City.  Warning Evelyn that she will be deserted by the Thaws, Hunchbacher offers Evelyn a job, but, unwilling to be exploited, she runs off.  When Evelyn goes to see Mrs. Thaw, however, the matron’s attempts to pay Evelyn off and force her to leave the country make her realize that Hunchbacher was correct.

Soon after, in Atlantic City, Hunchbacher introduces Evelyn as “the babe who left one guy pushing up daisies and the other in the bug house.” Her heart broken, Evelyn then swings in a red velvet swing over the heads of the roaring crowd.