The Most Expensive Celebrity Engagement Rings: Jackie O’s 40-Carat Harry Winston Sparkler, Grace Kelly’s Emerald-cut Cartier Bauble and More (2024)

It’s no surprise that celebrities have possessed some of the world’s most expensive engagement rings, from Kim Kardashian‘s cushion-cut stone to Jackie O‘s Harry Winston sparkler.

Some stars, like Paris Hilton and Mariah Carey, never made it down the aisle with their gigantic gems. Although relationships don’t always last, diamonds, as they say, are forever.

Here, WWD details 15 of the world’s most expensive engagement rings.

Kate Upton

Kate Upton became engaged to baseball player Justin Verlander in 2016. The model’s eight-carat round-cut diamond ring, designed by Anita Ko, is worth around $1.5 million.

Paris Hilton

Hilton’s third engagement was to actor Chris Zylka, who proposed with a 20-carat pear-cut diamond ring. After they broke off their engagement, the heiress refused to return the $2 million bauble because Zylka reportedly received it for free from a close friend, jeweler Michael Green.

Ciara

When footballer Russell Wilson proposed to Ciara in 2016, he gifted her a 16-carat round brilliant-cut diamond ring.

Blake Lively

Blake Lively’s pink diamond sparkler, given to her by Ryan Reynolds, features a seven-carat oval-cut stone set in a rose gold halo band. Worth approximately $2.5 million, the ring was designed by celebrity jeweler Lorraine Schwartz, who also happens to be a close friend of Lively’s.

Serena Williams

After Alexis Ohanian made $50 million from cryptocurrency investments, he used $3 million of the earnings to purchase a white diamond engagement ring for his wife-to-be, Serena Williams. Flanked by two smaller stones, its oval-cut centerpiece is a whopping 17 carats.

Kim Kardashian

Kardashian’s third husband, Kanye West, rented out San Francisco’s AT&T Park for his 2013 proposal. He popped the question with this 15-carat cushion-cut jewel, which was worth an estimated $4 million. Kardashian’s engagement ring was stolen in 2016 when robbers broke into her Paris hotel room. After eight years of marriage, Kardashian and West divorced in 2022.

Vanessa Bryant

Late basketball legend Kobe Bryant gifted his wife, Vanessa, a new engagement ring in the early 2000s. The eight-carat emerald-cut purple diamond, worth about $4 million, features an infinity band. It was custom-made by Rafinity, a now-defunct Los Angeles jeweler whose celebrity clientele also included Gwen Stefani, Halle Berry and Celine Dion.

Jennifer Lopez

The $4 million emerald-cut blue diamond marks Lopez’s first entry on the list. It was given to her by singer Marc Anthony, Lopez’s husband from 2004 to 2014. The 8.5-carat center stone is surrounded by white diamonds.

Paris Hilton

Before she tied the knot with businessman Carter Reum in 2021, Hilton was betrothed to Paris Latsis. The Greek shipping heir gave her a 24-carat emerald-cut diamond ring, reportedly worth $4.7 million. Latsis and Hilton began dating in late 2004, calling it quits just a month after their 2005 engagement.

Jennifer Lopez

Ben Affleck first proposed to Lopez with a 6.1-carat pink diamond worth $1.2 million, but he upgraded to an 8.5-carat cushion-cut green diamond for his 2022 proposal to the pop singer. Bloomberg estimates that the ring, which also features two white diamonds, is worth $5 million to $7 million.

Jennifer Lopez

Lopez’s priciest engagement ring came from Alex Rodriguez, whom she dated from 2017 to 2021. The couple revealed their engagement in 2019, with Lopez flashing an impressive $5 million ring gifted to her by the former baseball player. The emerald-cut stone was estimated to be between 15 and 20 carats.

Beyoncé

Jay-Z proposed to Beyoncé with a 24-carat rock. Featuring an emerald-cut diamond and a double infinity band, the ring reportedly cost around $5 million.

Mariah Carey

Mimi’s massive 35-carat ring was given to her by ex-fiancé James Packer, who paid an estimated $10 million for the emerald-cut gem. Carey was engaged to the Australian businessman from January to October 2016. She sold the ring for $2.1 million two years after their split.

Jacqueline Kennedy Onassis

Upon his engagement to Jackie, John F. Kennedy gave her a Van Cleef & Arpels ring with diamond and emerald jewels, each 2.8 carats. Jackie’s second husband, Greek businessman Aristotle Onassis, presented her with a 40-carat emerald-cut diamond by Harry Winston, which she stored in a bank vault. The ring fetched $2.6 million at a 1996 auction, but today, it’s worth about $20 million.

Grace Kelly

Kelly made headlines following her engagement to Prince Rainier III of Monaco. Cartier designed the actress’ stunning 10-carat emerald-cut ring, which is worth $44.3 million when adjusted for inflation.