All About Jackie Kennedy's 3 Engagement Rings (Including Her Dazzling 40-Carat Diamond)

From the historic ‘toi et moi’ JFK proposed with to the 40-carat diamond Aristotle Onassis chose.

• Jackie Kennedy was briefly engaged to stockbroker John Husted Jr. in 1952. Little is known about that engagement ring.
• In 1953, then-Senator John F. Kennedy proposed. The couple later picked out a diamond and emerald ring from Van Cleef & Arpels.
• In 1968, five years after JFK's death, Jackie married Aristotle Onassis. He proposed with a 40-carat marquise-cut diamond from Harry Winston.

As one of the most endearing American style icons of all time, it’s no surprise that Jackie Kennedy’s engagement rings are just as influential and inspirational as her wardrobe all these years later. The engagement rings she received from both John F. Kennedy and her second husband, Aristotle Onassis, have continued to inform the jewelry choices of modern-day brides, who look to evoke the former First Lady’s innately elegant and statement-making sensibility with their own baubles. While two-stone engagement rings may seem like a modern trend, Jackie wore one beginning in 1953. And though the public is most familiar with the former first lady's two marriages, not everyone knows that Kennedy (née Jacqueline Lee Bouvier) was actually engaged three times.

Little is known about her short-lived first engagement (or the ring).

In her early 20s, the New York-born fashion plate was first betrothed to a stockbroker John Husted Jr. after a whirlwind one month of dating. According to the book Jackie, Janet & Lee, at the couple’s engagement party in June 1952, both Bouvier and her mother, Janet, found out that Husted Jr.’s salary was ‘just’  $17,000 a year (the equivalent of $160,000 today) and were seemingly left unimpressed, People reported. 

The book’s author, J. Randy Taraborrelli, writes that the up-and-coming journalist soon ended things with Husted Jr.  by slipping her engagement ring off her finger and cooly dropping it into his pocket. To date, little to nothing is known about that ill-fated ring. 

It was Georgetown-based power couple Charles and Martha Bartlett who had first thought that Bouvier would hit it off with Massachusetts congressman John F. Kennedy. The couple invited both eligible parties to dinner at their home one night to sew the seed, according to CBS news. Bouvier, then a career-obsessed emerging on-air camera personality, was smitten. "He needed a gal. And we found him a hell of a gal,” the late, Pulitzer-prize winning journalist Barlett was quoted as saying. 

JFK proposed with a diamond and emerald toi et moi ring.

JFK proposed to Bouvier on June 24, 1953. Though it can't be confirmed, rumor has it that JFK popped the question at Martin’s tavern in Washington D.C. The restaurant has since christened booth #3 as ‘the proposal booth.’ But as for the ring? That reportedly came later. When the highly-watched couple officially announced their impending nuptials, Bouvier notably wasn’t wearing a ring.

The rock fitting of the would-be First Lady was eventually picked out at the Van Cleef & Arpels Fifth Avenue boutique in New York City. And word has it, it was actually selected by JFK’s father, Joe Sr. The ‘toi et moi’ dual stone design comprised a 2.84-carat emerald-cut emerald and a 2.88 carat emerald-cut diamond, writes Jay Mulvaney, who penned Kennedy Weddings. The show-stopping ring was reported by outlets to have cost up to $1 million at the time of purchase, according to Brides.

A decade later, fully settled into her role in The White House, Kennedy would reimagine and redesign the piece with the help of Van Cleef & Arpels, replacing the baguettes with 12 marquise-cut and round-cut diamonds that formed the shape of a laurel wreath resting underneath the larger stones. 

After JFK was tragically assassinated in 1963, the widow stopped wearing the ring in public. Like many of her most precious pieces, the symbolic and history-steeped engagement ring is in the permanent collection at the John F. Kennedy Presidential Library and Museum in Boston, where it occasionally goes on display. 

Aristotle Onassis proposed with a 40-carat marquise diamond.

In October 1968, the ‘Jackie O’ era officially began when Kennedy said ‘I do’ to her long-time friend, Aristotle Onassis. The small and intimate wedding, which took place on Onassis’ private island, came as quite a surprise to the world, as the Greek shipping magnate had previously dated her sister, Lee Radziwell.

Once again, her ring became the subject of immense public fascination. And for good reason: the mega-wealthy businessman popped the question with a staggering 40-carat marquise-cut diamond purchased from Harry Winston. Kennedy Onassis rarely wore the rock in public, preferring to keep it in a bank vault for safekeeping.  

Two years after Kennedy's death, the Lesotho III sold for $2.58 million at a Sotheby’s auction in 1996. (Far surpassing its valuation of $600,000!) The Los Angeles Times originally revealed that the infamous ring was purchased by Weight Watchers founders Albert and Felice Lippert on behalf of an anonymous purchaser who was never named in the media—meaning that there’s no trace of where the Lesotho III might be today.