San Francisco ad man Teddy Pierce is amused by, then obsessed with, a beautiful woman whose red dress goes whooshing over her head from a gust of wind, blowing her skirt and showing her red satin bikini panties while she crosses a grate. Teddy is happily married to Didi, but he cannot get this woman out of his mind. Encouraged by his friends Buddy, Joe and Michael, he tries to ask her for a date but mistakenly phones Ms. Milner, a plain ad-agency employee who is flattered by his interest.
Teddy ultimately does become acquainted with the woman in red, a model named Charlotte, going horseback riding with her and even inviting her to a relative’s party. He radically alters his wardrobe and begins using elaborate ruses to see Charlotte socially. Meanwhile, he incurs the wrath of Ms. Milner, whom he stands up.
Events come to a head in Charlotte’s high-rise apartment, where she invites Teddy into her bed. He is thrilled until her airline pilot husband suddenly comes home. Trying to escape, Teddy ends up on a ledge, where passersby below believe he is about to commit suicide, all captured on live television. He jumps out the window and waits to be caught by the firemen. While falling, Teddy starts to become interested in a newswoman who smiles at him.