The origin story of Edith Head, the quintessential Hollywood costume designer of the 20th century, is a tale of equal parts artistry and chutzpah. In 1923, when Ms. Head saw a job posting from Paramount seeking a costume sketch artist, she asked students at the art school where she was working to give her sketches that she could pass off as her own. The apparent versatility of her portfolio amazed the studio’s chief costume designer, Howard Greer.

When Ms. Head started at the job and her abilities weren’t quite as advertised, Mr. Greer told her he had always known she had borrowed the sketches. He hired her, Ms. Head recalled years later, because “anyone who had that much desire to get into the studio deserved the job.”

On Thursday, a dozen of Ms. Head’s sketches from the 1950s and ’60s (these are actually hers) are set to be sold by Doyle, an auction house on the Upper East Side of Manhattan. The lots include art from two of the most recognizable characters Ms. Head dressed: Grace Kelly’s Frances Stevens in “To Catch a Thief” and Kim Novak’s Madeleine Elster in “Vertigo.”

Over her career, which spanned five decades and hundreds of movies, Ms. Head received 35 Academy Award nominations and won eight of them. Her range was expansive, if often reliant on a snugly nipped waist.

Ms. Head, who died in 1981, concocted several ways to highlight the ambitious shoulders of Anne Baxter and Bette Davis in “All About Eve,” she made endless variations on a delicate little skirt suit for the heroines of Alfred Hitchcock nail-biters, and she designed full skirts that seemed entirely made of glitter for festive eyepoppers like “White Christmas.” She popularized the sarong, the toreador pant and other fashions from abroad for Western audiences. Still, she remained cleareyed about her limits with a resigned humor, famously saying, “You can lead a horse to water and you can even make it drink, but you can’t make actresses wear what they don’t want to wear.”