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5 Most Expensive Celebrity Engagement Rings of All Time: A Glimpse into Luxury

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More than Size: The Iconic Celebrity Engagement Ring

The most expensive celebrity engagement rings are really cultural entities carved in pop culture history rather than simply extravagant purchases. These glittering, mega-carat sparklers are worn by global stars and go on to spark endless fascination and media buzz. From Jennifer Lopez’s stunning collection to Kim Kardashian’s rings tied to a high-profile heist, these jewels are worth their weight. What brings together the most expensive celebrity engagement rings in a nutshell?

Time-honored treasures this trend harkens back decades, with Elizabeth Taylor’s self-touted “ice skating rink” and Jackie Kennedy Onassis’s 40-carat Harry Winston ring, laid up in a bank vault. Princess Grace Kelly’s 10-carat Cartier ring, which nowadays has a price tag on it of $38 million, created the standard. The modern celebrity continued that legacy of extravagant rings too valuable to be worn in public.

Jennifer Lopez's expensive engagement ring
Source: Jon Kopaloff/FilmMagic

Jennifer Lopez’s Amazing Ring Collection

This engagement ring was 8.5 carats radiant cut, surrounded by white diamonds Jonathan Lopez got for her in exchange with his ex-wife, Marc Anthony, and cost a whopping $4 million at the time of their marriage in 2004 to 2014. The 10-15 carat emerald-cut ring that Alex Rodriguez gave her in 2019 when proposing is rumored to have cost between $1 to $5 million but was never worn after separation from him in 2021.

The most iconic rings of hers, though, come courtesy of Ben Affleck: first, a 6.1-carat pink diamond by Harry Winston worth $2.5 million in 2002, and then an 8.5-carat green cushion cut diamond and two white diamonds in 2022, valued at $5-7 million as per Bloomberg. Clearly, these rings celebrate Lopez as a jewelry icon.

Kim Kardashian's expensive engagement ring
Source: Jason LaVeris/FilmMagic

Kim Kardashian’s Opulent and Stolen Rings

Like those engaged to Kanye West, Kim Kardashian’s engagement rings are equally extravagant. The ring that West presented her with would be an estimated $8 million engagement ring, a cushion-cut diamond of about 15 carats in size. This will be given to her daughter, North. A 20-carat ring was among the items heisted from a hotel in 2016 Paris, which only adds to the mystery. Such incidents make more headlines about Kardashian’s diamond rings, and they seal them as both rich and newsworthy.

Blake Lively expensive engagement ring
Source: Andrew Toth/FilmMagic

Blake Lively

Ryan Reynolds presented to Blake Lively a ring with an impressive weight and an even better status-changing paradigm in the paradigm shift that he made on the engagement ring. The 7-carat, oval-cut light pink diamond, set in a pavé diamond band made of rose gold, was crafted by Lorraine Schwartz and is estimated to be worth $2.5 million. An impressive event that Reynolds gave actually took the whole madness of oval-stone rings into the jewelry world, which is still enjoyably reigning up to this day. 

Kate Upton expensive engagement ring
Source: Getty Images

Kate Upton

Supermodel Kate Upton’s long-time love Justin Verlander popped the question back in 2016. The baseball player sealed the deal with an eight-carat round-cut diamond ring by Anita Ko that has an estimated value of around $1.5 million.

Ciara expensive engagement ring
Source: Wireimage

Ciara

Ciara, one who just loves to show off her diamond engagement ring, often very deliberately over her evening gloves on the red carpet, still manages to draw attention to it: A magnificent stone, presented to her by her husband-NFL star Russell Wilson-this is a stupendously lovely 16-carat round brilliant-cut diamond surrounded by two trapezoid-shaped diamonds and two pear-shaped ones. This engagement ring has a value of $2 million, making it a powerful and dazzling symbol of enduring love. 

Why These Rings Have Appeal in 2025

These engagement rings combine rarity with glamor, which is why they continue to attract in 2025. The stories-the heists, the proposals, the cultural impact-keep them alive. For luxury jewelry enthusiasts, these rings symbolize the epitome of glamour in design and value.

Shop Celebrity-Inspired Jewelry

Dreamy for these rings? Make special requests for custom designs from jewelers like Harry Winston or Lorraine Schwartz. For some affordable ideas, search for similar styles online. Keep an eye on trending celebrity jewelry in 2025!

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