The editors of Harper’s Bazaar were flummoxed. They had invited Truman Capote, renowned for stories, screenplays, and the autobiographical novel Other Voices, Other Rooms, to write about the New York of his youth. He replied with a long story that looked back on the early years of World War II, a time of soldiers and sailors embarking for battle, a whirl of smoky barrooms and people you would never see again. But daringly, he put at the center of the story a young woman, not yet out of her teens, whom Capote later characterized as “an American geisha”—not exactly a prostitute but not exactly not a prostitute, either.

Added to that were hints of nonheteronormative love between men and women, war profiteering, and the la dee da of people who ate in swanky venues while everyone else made do with rations. It was not what a family publication would find suitable back in the mid-1950s, which, though not as gray a time as we imagine it to be, had its conventions. William Randolph Hearst Jr. himself is said to have ordered that Capote’s manuscript be sent back for retooling. Capote declined, instead taking Breakfast at Tiffany’s to Rust Hills, the legendary fiction editor at Esquire. The story was published 60 years ago, in 1958, and then gathered into a book by that title with three accompanying short stories.

Breakfast at Tiffany's cover Capote may have aimed to shock with the premise that his heroine was a sex worker, but she was in some ways more an ingénue than the lead in his posthumously published Summer Crossing, Grady McNeil. In other ways, though, Holly was a kind of Gatsby for the postwar era: As the story unfolds, we learn that she had been born in some dusty Texas town, married at 14, and then made a break for the big city—but with even greater ambitions in mind. Says her much older abandoned husband, who tracks her down in New York after five years of looking, “She knew good and well what she was doing when she promised to be my wife and the mother of my churren. She plain broke our hearts when she ran off like she done.”

Holly was born to break hearts. Even the narrator, a writer who, with his jars of pencils to sharpen and stories to wrestle down on paper and no fixed interest in the ways of the ordinary world, falls in love with her a little. As the story closes and Holly works her way toward fame and fortune—and then, eventually, disappearance—we are all in love with her a little even though we know that, like cigarettes and too many highballs, she’s not good for us.

Truman Capote, who would go on to shock still further with In Cold Blood, meant for his Cinderella story to go to Marilyn Monroe. When the movie version appeared in 1961, scrubbed clean of most of its sub rosa elements, the aristocratic Audrey Hepburn stood in Monroe’s place, her eye set on fairy-tale, G-rated happiness. It wasn’t what Capote planned—but then, almost nothing was about Breakfast at Tiffany’s, a book that holds up six decades on.

Gregory McNamee is a contributing editor.