The Secret Connection Between Grace Kelly and Jackie Kennedy

Updated: Nov. 03, 2022

One man. Two women. Two love affairs, but only one was romantic. The other was pure fashion.

Grace Kelly and Jackie Kennedyshutterstock (2)

Jacqueline Kennedy’s look was synonymous with sophistication and exquisite taste; so was Grace Kelly’s—and this was no accident. Both women turned to the same man to get their timeless style—noted Russian fashion designer, Oleg Cassini. Here’s how it happened.

Oleg and Grace

Having been captivated by Grace in her role in the 1953 film, Mogambo, Cassini wooed the actress with a daily bouquet of red roses until she finally agreed to have lunch with him. Not only did Cassini begin to dress the actress, but the two began dating. Cassini created “the Grace Kelly Look,” as he called it, transforming the glamorous actress’s look from “school teacher” to something a little sexier. In 1954, they became engaged to be married, although the engagement was broken off due to pressure from the actress’s parents—they didn’t like that he’d been married twice before and had a reputation of being a Cassanova. In 1956, Grace Kelly married Prince Rainier of Monaco.

Oleg and Jackie

After Cassini met Jackie, she began to consult him about fashion. “I dressed Jackie to be a star in a major film, which she was, the most famous first lady of all time,” Cassini once said, and Mrs. Kennedy agreed, “Oleg dressed me for the part.” Over the years, Cassini created more than 300 outfits for Jackie, whom he regarded as American royalty, and drew on his experience with Kelly to give the First Lady her stunning look.

Grace, Jackie, and John F. Kennedy

After her marriage to the Prince of Monaco, Princess Grace came to favor Givenchy over Cassini: In this interview, which Kelly did shortly after JFK’s death, she discusses the president’s style and youthfulness and her evolving sense of fashion. She also discusses the time Jackie convinced Grace to visit John in the hospital in 1954 while he was recovering from back surgery in New York—the first time Grace met the man who would become president. (For the meeting she dressed as a nurse as a prank!)

Of course, there are some who insist that before he married Jackie, John Kennedy had once been in love with Grace Kelly. But we’ll never get firsthand confirmation: Princess Grace of Monaco passed away on September 14, 1982 (in a tragic car accident in her adopted country of Monaco), and Jacqueline Kennedy Onassis passed away in 1994 (of cancer). Next, don’t miss these 13 rarely seen photos of Jackie Kennedy.