When Oleg Cassini first met with Jackie Kennedy, she was sitting in a hospital bed soon after giving birth to her son John, surrounded by “sketches from French and Italian and American designers,” he told PEOPLE in 2001. “They were all vying for her attention.” Looking for guidance, Kennedy turned to Cassini, a friend of her father-in-law Joe, in a move that would create fashion history. “I suggest you forget about representing the look of the moment,” he recalled saying to her. “You should have your own look.”
The look she chose was Cassini’s. Hiring him to dress her almost exclusively, the First Lady ultimately commissioned some 300 items from the designer, including her most iconic outfits: the sheath dresses, the Grecian gowns and the ever-present pillbox hat (which Halston invented but Cassini, by way of Kennedy, popularized). So influential was the collaboration that when Cassini died on March 17 three weeks shy of his 93rd birthday following complications from a ruptured blood vessel, it was his work for Kennedy that remained his most enduring legacy.
And yet Cassini remained a vital fashion force even in his later years; among his final designs were Kim Basinger’s costumes for the upcoming film The Sentinel. “It gave me insight into how Jackie Kennedy and Grace Kelly must have felt each time Oleg worked with them,” Basinger says. “He was a lovely gentleman.” On March 10, the day before he fell ill, Cassini spent the day in business meetings before heading with his wife, Marianne Nestor (whom he married in 1971), to their weekend home in Oyster Bay, N.Y. “We had a lot of laughs that night,” she says. The next morning, however, “He said, ‘I have a terrible headache,'” recalls Nestor, who took him to the hospital, where doctors diagnosed the hemorrhage. “It was like a bullet in the head. He never made it back.”
The son of a Russian diplomat and an Italian countess, Cassini began his career as a Hollywood costumer before launching his own line in 1950. His air of sophistication won him wealthy clients—and led to romances with actresses like ex-wife Gene Tierney (with whom he had two daughters) and ex-fiancée Grace Kelly, whom he said he took from “the schoolteacher look” to “elegant, subdued dresses.”
Later, Cassini became one of the first designers to license his name, which is now found on everything from swimsuits to cars to a popular line of wedding dresses. But if there was a secret to his success, it was a simple one, he said: “I always made women look their best.”