When we talk about the Jackie Kennedy engagement ring, most people picture the same thing: that shimmering green-and-white masterpiece. But here’s the thing. There wasn’t just one "Jackie O" ring. Depending on who you ask—or which decade of her life you’re looking at—the answer changes.
Jackie basically reinvented herself three times, and her jewelry did the exact same thing.
Most folks don't realize that when John F. Kennedy actually proposed in 1953, he didn’t even have the ring yet. Imagine that. One of the most powerful men in the world, a future president, popping the question without the "ice" to back it up. Jackie later told reporters they’d looked at dozens of options but hadn't found the "right type." Eventually, they landed on a Van Cleef & Arpels stunner that would go on to change jewelry trends for the next seventy years.
The Ring That Started the "Toi et Moi" Craze
The first real Jackie Kennedy engagement ring was a "Toi et Moi" (You and Me) design. It’s a style that features two main stones sitting side-by-side.
Honestly, it was pretty daring for the 1950s. Most women back then were wearing simple solitaire diamonds. Jackie’s ring featured a 2.84-carat emerald-cut emerald and a 2.88-carat emerald-cut diamond. It was flashy but sophisticated. Some historians say JFK’s father, Joe Kennedy Sr., actually picked it out at the Van Cleef & Arpels boutique on Fifth Avenue.
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Classic Joe. He was always curate-ing the family image, even down to the gems on his daughter-in-law's finger.
Initially, the stones were flanked by simple tapered baguettes. It was sleek. It was Art Deco. But it didn't stay that way. By 1962, Jackie was the First Lady, and she decided the ring needed a "promotion" to match her new status. She sent it back to the jeweler and had the baguettes replaced with 2.12 carats of marquise and round diamonds. The new design looked like a laurel wreath, wrapping around the emerald and diamond. It turned the ring into an 8-carat powerhouse.
Why It Still Matters in 2026
You’ve probably seen "Toi et Moi" rings all over Instagram or Pinterest lately. Celebs like Megan Fox and Ariana Grande have brought the look back in a big way. But Jackie was the blueprint.
The mix of a colored gemstone with a diamond is a vibe that just doesn't quit. It’s personal. It’s less "cookie-cutter" than a massive rock on a thin band.
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If you're looking for a ring today, here’s what you can learn from Jackie’s choice:
- Emeralds are soft. If you’re active with your hands, an emerald might chip. Jackie was notoriously discreet with hers, often turning the stones inward or wearing gloves.
- Redesigning is okay. You aren't stuck with your original setting forever. Jackie’s 1962 upgrade proves that as you evolve, your jewelry can too.
- Proportions are everything. The 2.8-carat size was substantial but didn't look like a "costume" piece on her hand.
The "Other" Engagement Ring: The 40-Carat Monster
We can’t talk about the Jackie Kennedy engagement ring without mentioning the one that came after JFK. When she married Aristotle Onassis in 1968, the world basically lost its mind.
"Jackie O" was born. And Onassis didn't mess around.
He gave her the Lesotho III, a 40.42-carat marquise-cut diamond from Harry Winston. It was one of 18 stones cut from a massive 601-carat rough diamond found in South Africa. It was so big and so valuable that Jackie supposedly only wore it twice. The rest of the time? It sat in a bank vault in New York.
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Sorta makes you wonder what the point is, right? Having a ring that’s too famous to actually wear.
After she passed away in 1994, that 40-carat rock sold at a Sotheby’s auction for $2.58 million. Even more wild? The buyer remained anonymous, and the ring hasn't been seen in public since.
Where is the JFK Ring Now?
If you want to see the original emerald-and-diamond ring, you don’t have to hunt down a secret billionaire. It’s actually sitting in the John F. Kennedy Presidential Library and Museum in Boston.
It’s part of the permanent collection. It’s a bit of a pilgrimage for jewelry nerds. Seeing it in person, you realize it’s not just a piece of jewelry; it’s a tiny, sparkling piece of American history.
Quick Facts for the Jewelry Obsessed
- Jeweler: Van Cleef & Arpels (JFK) / Harry Winston (Onassis).
- Carat Weight: The JFK ring grew from roughly 6 carats to 8 carats after the redesign.
- The Metal: The original was set in a mix of yellow gold and platinum.
- The Trend: Jackie is credited with making the "Toi et Moi" style a staple for high-society engagements.
When you're choosing your own ring, don't feel pressured by the "standard" diamond solitaire. Jackie’s legacy shows that the most iconic pieces usually break the rules. Whether it's mixing stones or changing the setting ten years later, your jewelry should tell your story, not just follow a trend.
If you’re planning a ring purchase or a redesign, your next step should be to look into "bypass" settings. This is the specific structural style Jackie used to nestle those two stones together. It’s a great way to make a ring feel architectural and unique without needing a 40-carat budget. Search for "vintage bypass engagement rings" to see how that 1950s look can be modernized for today.