Most Valuable Celebrity Engagement Rings of All Time

Year Purchased: 2002
Occasion: Engagement to Ben Affleck 
Est. Value: $1.7 million*

Jennifer Lopez has had some high-profile relationships in her time, but her romance with Ben Affleck was the talk of the noughties. Ben proposed to the iconic singer in 2002, and he wasn’t afraid to spend some serious money on the ring. The pink diamond reportedly cost $1.7 million. 

©Featureflash Photo Agency/Shutterstock | ©Kevin Winter/Getty Images

While the marriage would never go ahead, J-Lo admitted years later that she’s still impressed with the ring to this day. Lopez would go on to date other big names, including Marc Anthony and Alex Rodriguez. In 2021, rumors of Affleck and Lopez reconciling were all over the headlines. 

Year Purchased: 1955
Occasion: Engagement to Prince Rainier III of Monaco 
Est. Value: $4.3 million*

For many movie fans in the ‘50s, Grace Kelly was living a true fairytale. The starlet had a successful career in Hollywood before she met Prince Rainier III of Monaco in 1955 while promoting one of her films. In less than a year, the Prince proposed to Kelly and the rest was history. 

Grace Kelly @baunat / @juliajones28 / Pinterest.com

Kelly was actually lucky enough to get two rings, both from Cartier. The second one was an emerald-cut 10.48-carat diamond worth over $4.3 million. By all accounts, the CBS Paramount star and her prince lived a very charmed life. 

Year Purchased: 2018
Occasion: Engagement to Chris Zylka  
Est. Value: $2 million*

Despite being engaged four times, Hilton has yet to actually make it down the aisle. There’s no denying that Hilton has great taste when it comes to rings though. In 2018, she said yes for the third time to actor Chirs Zylka. Zylka did not spare any expense, gifting Paris a pear-cut giant diamond. 

Paris Hilton @ParisHilton / Twitter.com | @CosmopolitanMx / Pinterest.com

The ring allegedly cost $2 million, so it’s hardly surprising that Hilton said yes. The couple never said “I do” as they split up ten months later. Paris got engaged for the fourth time in 2021 to Carter Reum, who presented the heiress with a $1 million custom ring.

Year Purchased: 1953
Occasion: Engagement to JFK
Est. Value: $1 million*

The story of Jackie and John Kennedy is one tainted with tragedy, but back when John first popped the question in 1953, they had no idea what would befall them. Jackie was head over heels for her beautiful engagement ring which she picked out from Van Cleef & Arpels in New York. 

Jackie Kennedy @fashion9852 / Pinterest.com

Consisting of diamonds and emeralds, the ring wasn’t exactly traditional, although it was beautiful. Unlike some other brides, Jackie was never one for showing off the jewel, however, after JFK made it into the White House she had the ring revamped by Van Cleef & Arpels, adding marquise diamonds. 

Year Purchased: 2020
Occasion: Engagement to Blake Shelton
Est. Value: $500,000*

Country icon Blake Shelton and pop rock queen Gwen Stefani may seem like an odd couple, but the two have been dedicated to one another since they first started dating in 2015. Stefani, who was previously married to Gavin Rossdale, said yes when Blake popped the question in October 2020. 

Gwen Stefani @aguasd / @eentertainment / Pinterest.com

As you might imagine, Blake didn’t get down on one knee empty handed. He proposed to Gwen with a very expensive looking square-cut diamond ring. As it turns out, the rock is thought to be worth at last half a million dollars, if not more. 

Year Purchased: 2005
Occasion: Engagement to Tom Cruise 
Est. Value: $2 million*

Tom Cruise has been one of Hollywood’s most bankable stars for decades now, which means fans are just as invested in his private life as they are his on-screen work. Cruise was famously married to Nicole Kidman, but after that chapter of his life ended, he found love again with Dawson’s Creek actress Katie Holmes. 

Katie Holmes @lonabega / @aogjewelry / Pinterest.com

Despite the age gap, Holmes and Cruise seemed to fall hopelessly in love in 2005. Tom proposed to Katie just seven weeks after they met, presenting her with a 5.5.-carat oval diamond that had another splattering of diamonds thrown in for good measure. The ring was valued at $2 million.

Year Purchased: 2016
Occasion: Alexis Ohanian 
Est. Value: $3 million*

Tennis genius Serena Williams has a net worth of $210 million, making her one of the richest players ever to step out on the court. Not only is Williams financially rich, but her love life has prospered, too. Serena found her match in Reddit co-founder Alexis Ohanian. 

Serena Williams @soynadie / @Love_Wedding_Bands / Pinterest.com

Ohanian asked the icon to marry him in 2016, and as you might expect, the ring was more than worthy. The huge rock is thought to be around 12 carats and cost Alexis $2 million. Considering the average engagement ring costs $6,000, Serena really landed on her feet with that one.  

Year Purchased: 2009
Occasion: Engagement to Jared Kushner 
Est. Value: $500,000*

Years before Ivanka Trump would become a presidential aide, she was a wealthy heiress marrying Jared Kushner. Kushner and Ivanka got engaged back in 2009, but Jared picked the ring wisely, opting for a classic diamond that turned heads – and cameras.  

Ivanka Trump @ella777111 / Pinterest.com | ©Debby Wong / Shutterstock.com

The stunning jewel reportedly cost $500,000. Ivanka rarely wears it these days and doesn’t always wear her wedding ring, either. That doesn’t mean that there’s trouble in paradise, though. Ivanka seems just as comfortable wearing it as she does without it.

Year Purchased: 2005
Occasion: Engagement to Prince Charles 
Est. Value: $100,000*

Prince Charles’ love life has been tumultuous to say the least. Even though Charles married Diana, his heart always belonged to his ex-love, Camilla Parker-Bowles. The two had a highly-publicized affair. After his divorce, Charles was free to pursue an official relationship with Camilla. 

Camila Parker-Bowles @white4397 / Pinterest.com | ©James Pearce / Shutterstock.com

He finally proposed to her in 2005, but the ring wasn’t simply one that he picked up from a jeweler. Camilla’s ring was actually gifted to Charles by the Queen Mother. The art deco ring has a 5-carat diamond as its showstopper and is reportedly worth around $100,000. 

Year Purchased: circa 2008
Occasion: Engagement to Jay-Z
Est. Value: $5 million*

When Beyonce married Jay-Z in 2008, it was a lowkey affair that the couple didn’t even announce. They quietly picked up a marriage license and tied the knot without the media circus that could have followed. In fact, fans didn’t even know they were engaged. 

Beyonce @bernartchantal / @dianebusza22 / Pinterest.com

When the truth was revealed all eyes were on the rock. Jay-Z didn’t hold back when it came to the incredible diamond, reportedly shelling out $5 million to get his wife-to-be a truly phenomenal piece of jewelry. It’s thought to be a 24-carat masterpiece, making Beyonce’s ring one of the most expensive engagement rings in Hollywood history. 

Year Purchased: 2005
Occasion: Engagement to Jordan Bratman  
Est. Value: $2.5 million*

Christina Aguilera has hit all the right notes in her career, amassing a fortune of over $140 million. The songstress tied the knot in 2005 to Jordan Bratman. Although the marriage itself ended in 2011, Aguilera was happy at the time Bratman popped the question, freely showing off the ring to photographers. 

Christina Aguilera @zimbio / Pinterest.com

The Sony star was more than happy with her vintage-inspired $2.5 million diamond, just like most would be. It fit her noughties style to a T, matching her Marilyn Monroe-inspired aesthetic. The marriage may have turned sour, but the ring stayed bright and shiny. 

Year Purchased: 2012
Occasion: Engagement to Justin Theroux 
Est. Value: $500,000*

Jennifer Aniston has forged a glittering career for herself, but she hasn’t always been as lucky in love. The Friends star famously married Hollywood heartthrob Brad Pitt in the ‘90s, only for him to up and leave her for Angelina Jolie. Aniston found love again and got engaged to Justin Theroux in 2012. 

Jennifer Aniston @lavidabaker / @arabiaweddings / Pinterest.com

The marriage would be short-lived, but luckily for the Warner HBO star, diamonds last forever. Justin proposed with this giant rock that reportedly cost $500,000. That’s a lot of money by anyone’s standards, even if Jen is worth $212 million.  

Year Purchased: 2020
Occasion: Engagement to Dion Hamilton  
Est. Value: $100,000*

Jourdan Dunn has made a name for herself as a model and actress, so the British beauty has a solid fanbase. Her followers were elated in 2020 when she announced that her longtime partner Dion Hamilton had finally put a ring on it. 

Jourdan Dunn @xakar6 / @hellomag / Pinterest.com

Dunn wasn’t shy about posting pictures of the 2-carat oval diamond on Instagram. The rock is thought to be worth around $100,000, but judging by the smile on Jourdan’s face, it was worth every penny. Something tells us it will be in the family for many years to come! 

Year Purchased: 1968
Occasion: Gift from Richard Burton 
Est. Value: $1 million*

Elizabeth Taylor was just as well-known for her love of jewels as she was for her acting prowess. Her relationship with Richard Burton was also infamous in its own right. In 1968, Burton managed to buy the Krupp diamond for Liz, who swiftly had it set into a ring. 

Elizbeth Taylor @atticatalley / Pinterest.com

The Sony actress was so in love with her $1 million piece that she flaunted it every chance she could. Despite the fact that Burton and Taylor married four years prior to the Krupp diamond falling into their possession, the ring is often cited as Liz’s “engagement” ring.