The Most Eye-Wateringly Expensive Vintage Celebrity Engagement Rings

Nothing is ever too much for the people you love, and for celebrities, this is often brought to a whole different level. The days of Old Hollywood have shown that when it comes to wedding rings, it's time to pull out all the stops for your beloved. And while we've taken a look at some of the most iconic Old Hollywood engagement rings in living memory, some of these bands are remembered not just for their beauty, but for their eye-watering price tags.

From Grace Kelly to Elizabeth Taylor, these recognizable names brought both their acting talents and their love lives to the forefront. The sheer extravagance of today's celebrities pales in comparison to the glamour of Hollywood's Golden Age, when glittering statement pieces and heirloom jewels were shown off and collected. And for the celebrities of the past, it seems there's no better way to herald a new stage in life together than a shining rock worth millions.

One of the most well-known figures in Old Hollywood, Grace Kelly was not only a darling of Alfred Hitchcock's films, but she also managed to bag a Prince. Prince Rainier III of Monaco, to be precise. And as a blue-blooded royal, he could afford to purchase the best engagement ring money could buy. Grace Kelly's whopping 10.48 carat engagement ring became legendary and cost the Prince $4.6 million to obtain from Cartier. The ring had a large, oval-shaped emerald-cut diamond set in a gold band, one that could be seen in Kelly's last-ever film, "High Society".

However, this was the second engagement ring the Prince gave Kelly. The first engagement ring was, in fact, considered far more priceless than the second, due to its historic value. The stones used in the first ring were heirloom pieces owned by the House of Grimaldi. As such, there can be no doubt that Grace Kelly might have received one of the most expensive engagement rings ever in Hollywood. 

Although not technically Hollywood royalty, from her fashion choices to general notoriety, Jackie Kennedy was one of America's most famous First Ladies. So it's fitting that the dark-haired beauty received a truly gorgeous engagement ring from her first husband, President John F. Kennedy. The latter, who wasn't yet elected President when he proposed, bought a $1 million Van Cleef & Arpels ring and proposed to Jackie in 1953. The ring bears a unique corded shape that's studded with diamonds, with the cherry on top being the 2.84-carat emerald and 2.88-carat diamond placed next to each other.

The $1 million ring would be worth a hefty $12.5 million in 2026, but unlike the other rings in this list, Jackie's engagement ring from JFK wasn't put up for auction after her death. And it's understandable why, due to its historical weight. Jackie's engagement ring has been given to the John F. Kennedy Presidential Library and Museum, where it remains today.

Aside from being known for her iconic role as Cleopatra and her many marriages, Elizabeth Taylor was also a huge fan of expensive jewelry. And this was something her famous actor husband, Richard Burton, knew very well. "The only word Elizabeth knows in Italian is 'Bulgari'," Burton once said (per People), implying the "A Place in the Sun" star's penchant for the lavish life. But that didn't stop him from giving Taylor the very best.

The "Anne of the Thousand Days" actor forked over $307,000 ($2.9 million in 2026) at an auction in 1968 to buy his beautiful wife what was then known as the Krupp Diamond. The massive diamond was an eye-watering 33.19 carats and was so synonymous with the legendary star that it was renamed the Elizabeth Taylor Diamond. After Taylor's passing, the diamond was sold at a Christie's auction, its worth more than tripled to net over $8.8 million.

After the tragic assassination of her first husband, President John F. Kennedy, Jackie Kennedy managed to find love again with Greek shipping tycoon Aristotle Onassis. The billionaire went straight to Harry Winston, where he purchased a jaw-dropping 40.42 carat ring for an undisclosed price that definitely involved a lot of zeroes. It's quite difficult to find a picture of the ring, as Jackie herself chose to store it in a vault rather than wear the massive ring in public. 

While her ring from her first husband became a historical relic, her second engagement ring found its way to a Sotheby's auction in 1996 after her passing. The ring ended up netting the auction house $2.6 million, and when adjusted for inflation, is an estimated $5.6 million in 2026. It's unknown whether Onassis or Kennedy selected the ring, but whoever did surely had expensive taste.

Over a century ago, Wallis Simpson's name dominated the headlines in British newspapers. Then-King Edward VIII was infatuated with her, and ultimately gave up the throne to be with her. But before he abdicated in 1936, the British royal bought Wallis Simpson an engagement ring which proved to be a royally iconic piece of jewelry. Naturally, as a monarch, Edward VIII spared no expense and personally gave the specifications for Simpson's engagement ring to Cartier. 

The result was a 19.77-carat emerald ring with a romantic inscription carved into the gold band that undoubtedly cost a pretty penny. Naturally, due to its historical value, the ring fetched a high price when it was auctioned off at Sotheby's in 1987. The auctioneer called out the figure at $1.98 million, which would be a staggering $5.8 million in 2026. In our estimation, it certainly deserves a spot in our guide to the British royals' most gorgeous engagement rings, and a well-deserved nod as one of the highest amounts a royal has ever spent on a ring.