A Journey Through the Most Iconic Celebrity Engagement Rings
The modern-day fairy tale doesn’t always begin in a faraway castle. Often, it starts under the flashbulbs of Hollywood, inside royal palaces, or in the quiet intimacy of private proposals that become headlines the moment they’re revealed.
Celebrity engagement rings have become symbols of glamour, love, and enduring style. More than glittering tokens of commitment, these pieces offer insight into the personalities, values, and romances of the people who wear them.
Whether it’s the grandeur of royal diamonds or the sheer scale of Hollywood stones, engagement rings have long carried stories that extend far beyond the vows. According to With This Ring, The Ultimate Guide to Wedding Jewelry by Penny Proddow and Marion Fasel, these rings have sparked trends, stirred public imagination, and deepened pop culture’s fascination with famous love affairs.
Let’s journey through time to revisit the most captivating engagement rings of celebrities and royals—and what these iconic stones reveal about love, power, and personality.
Grace Kelly and Prince Rainier: From Simplicity to Cinematic Sparkle
When Prince Rainier III of Monaco decided to propose to Hollywood star Grace Kelly, he initially offered her a modest yet meaningful eternity band of rubies and diamonds—echoing the red and white colors of the Monegasque flag.
At a press conference on January 5, 1956, at Kelly’s family home in Philadelphia, the couple revealed their engagement. Photographers eagerly captured close-ups of the elegant ring.
But the prince quickly realized that in Hollywood, where diamonds dazzled in every scene, his initial choice might pale in comparison. During a visit to Los Angeles, Prince Rainier saw the enormous rings gracing the fingers of other actresses. He sent word to Cartier in Paris to design something grander.
The result? A 12-carat emerald-cut diamond flanked by two baguettes—a ring fit not just for royalty, but also for the silver screen. Grace wore this iconic piece while playing Tracy Lord in High Society, allowing life and art to blend beautifully.
The ring made headlines again as she boarded the Constitution cruise liner en route to Monaco, where the real-life fairy tale would unfold.
Queen Elizabeth II and Prince Philip: Royal Simplicity with Family Roots
In a love story steeped in tradition and duty, Prince Philip designed a ring for then-Princess Elizabeth using diamonds from a tiara that belonged to his mother, Princess Alice of Battenberg.
With help from his uncle, Lord Mountbatten, and London jeweler Philip Antrobus Ltd., he created a timeless design: a 3-carat round-cut diamond flanked by smaller stones, all set in platinum.
When he proposed on July 8, 1947, there was one minor hiccup—the ring didn’t fit. It had to be resized just in time for the official engagement announcement at a Buckingham Palace garden party.
While understated compared to modern celebrity standards, the ring reflected the young couple's devotion and the refined elegance of royal tradition.
Elizabeth Taylor: The Queen of Diamonds
No one quite embodied Hollywood glamour like Elizabeth Taylor, and her jewelry collection mirrored her larger-than-life persona. Her third husband, producer Mike Todd, proposed with a staggering 29.4-carat emerald-cut diamond ring, which she jokingly referred to as her “ice skating rink.”
Though she was still married at the time, the ring foreshadowed a whirlwind romance that culminated in a 1957 wedding in Acapulco.
But that wasn't the end of Taylor’s diamond legacy. Her legendary love affair with Richard Burton would introduce even more iconic gems—like the 33.19-carat Krupp diamond and the 69.42-carat Taylor-Burton diamond—although neither were engagement rings.
Instead, Burton gifted her a Bulgari emerald-and-diamond necklace and a pavé-set wedding band, further immortalizing their tempestuous yet passionate relationship.
Eleanor and Franklin D. Roosevelt: A Quiet Classic
Before political power, there was youthful romance. When Franklin Roosevelt proposed to his fifth cousin once removed, Eleanor, he selected a 3.4-carat cushion-cut diamond from Tiffany & Co.
The ring, set in gold with intricate platinum and diamond details, was a perfect blend of luxury and refinement. Presented to her on her birthday in 1904, Eleanor was so enchanted she wrote him that night, saying, “You could not have found a ring I would have liked better.”
Edward VIII and Wallis Simpson: Love Beyond the Crown
Perhaps no engagement ring in history has carried as much political weight as the one King Edward VIII gave to Wallis Simpson.
The ring, made by Cartier, featured a 19.77-carat emerald mounted in platinum. Engraved inside was a cryptic date: “We are ours now 27 X 36”—marking October 27, 1936, the start of Wallis’s divorce proceedings. The king’s proposal created a constitutional crisis, ultimately leading to his abdication.
The couple married in exile, but their love endured. On their twentieth anniversary, Wallis had the ring remounted but kept the original engraved setting until her death.
Marilyn Monroe and Joe DiMaggio: Diamonds and Drama
Joe DiMaggio’s proposal to Marilyn Monroe in 1954 came with a platinum eternity band set with 36 baguette-cut diamonds—an elegant symbol of enduring love. Though their marriage lasted only nine months, the ring remains one of the most iconic in Hollywood history.
Monroe’s understated chocolate suit and DiMaggio’s dark blue tie at their civil ceremony offered a sharp contrast to the sparkle of the ring and the media frenzy outside.
Audrey Hepburn and Mel Ferrer: Understated Elegance
True to her timeless style, Audrey Hepburn’s engagement ring was a study in sophistication. Mel Ferrer proposed with an eternity band of baguette-cut diamonds from Gübelin of Zurich.
For the wedding ceremony in Switzerland in 1954, Ferrer gave Hepburn two slim bands—one in white gold, the other in rose gold—matching the actress’s minimalist aesthetic. She wore them alternately, always effortlessly chic.
Jacqueline Kennedy and JFK: Politics and Panache
John F. Kennedy knew how to make a statement. When he proposed to Jacqueline Bouvier in 1953, it was with a Van Cleef & Arpels ring featuring a 2.88-carat diamond and a 2.84-carat emerald, set in a crossover design.
Jackie, ever the style icon, later redesigned the ring, replacing its baguette accents with marquise and round diamonds to reflect the First Lady’s evolving aesthetic during her White House years.
Frank Sinatra and Mia Farrow: Glamour and Gossip
On the Fourth of July weekend in 1966, Frank Sinatra proposed to Mia Farrow with a 9-carat pear-shaped diamond from Ruser, a famed Beverly Hills jeweler. The New York Post ran the headline: “Sinatra Buys Mia the Ring.”
Fifteen days later, they married in Las Vegas. To celebrate their whirlwind romance, Sinatra also gave Farrow a dazzling double-row diamond bracelet.
Victoria and David Beckham: A Stylish Love Story
When football star David Beckham met Victoria Adams—aka Posh Spice—in 1997, it was instant chemistry. Beckham proposed less than a year later with a 3-carat marquise-cut diamond on a yellow gold band from Boodle & Dunthorne.
True to her independent spirit, Victoria also gave her fiancé a Van Cleef & Arpels engagement ring, ensuring they both sparkled.
The couple, always style icons, also exchanged matching gold Rolex watches. Their 1999 wedding at a 15th-century Irish castle solidified their status as a power couple—and trendsetters for dual-ring engagements.
Will Smith and Jada Pinkett: A Ring with Humor and Heart
When Jada Pinkett and Will Smith decided to marry, they selected a ring together—a massive pear-shaped diamond. “It is a big ol’ ring,” Jada said in an interview.
She admitted that Will wanted an even larger one, joking that had he picked it alone, it would’ve been the size of a sugar bowl. The couple tied the knot on New Year’s Eve in 1997, with a ring as bold and radiant as their love.
More Dazzling Icons
Kim Kardashian and Kanye West
When Kanye West proposed to Kim Kardashian in 2013, he did so with a 15-carat cushion-cut diamond designed by Lorraine Schwartz.
Set in a thin platinum band to maximize the diamond’s brilliance, the ring was unveiled in a dramatic stadium proposal complete with fireworks and a live orchestra.
Meghan Markle and Prince Harry
Prince Harry designed Meghan Markle’s ring with love and legacy in mind. The central diamond was sourced from Botswana—a place dear to the couple—while the side stones belonged to Princess Diana.
The original gold band was later replaced with a thinner, more modern design, still keeping the symbolic elements intact.
Blake Lively and Ryan Reynolds
Blake Lively’s pink oval diamond from Lorraine Schwartz set a trend for non-traditional stones. Estimated at 12 carats and mounted on a rose gold band with pavé diamonds, it’s an embodiment of vintage glamour and modern romance.
Beyoncé and Jay-Z: Flawless and Fierce
When music mogul Jay-Z proposed to Beyoncé in 2007, he did so with a ring that screamed perfection. Designed by Lorraine Schwartz, the emerald-cut diamond is estimated at 24 carats and valued at over $5 million.
The flawless center stone is set in a split-shank platinum band, and the whole piece exudes both glamour and power—just like the couple. Beyoncé often wears the ring sparingly, reserved for special occasions due to its sheer size and value.
Angelina Jolie and Brad Pitt: Custom Collaboration
When Brad Pitt proposed to Angelina Jolie in 2012, he collaborated with jeweler Robert Procop to design a ring that took over a year to perfect. The centerpiece was a large tablet-shaped diamond flanked by graduated baguette diamonds, each cut to match the curve of Jolie’s finger.
The ring was estimated at around 16 carats and valued at $250,000. Although their relationship later ended, the ring remains a testament to their custom-tailored romance and attention to detail.
Jennifer Lopez: A Timeline of Iconic Rings
Jennifer Lopez has received several jaw-dropping engagement rings over the years. Among the most talked-about:
From Ben Affleck (2002): A 6.1-carat pink diamond from Harry Winston that reportedly cost $2.5 million. This ring ignited the trend for colored engagement stones.
From Marc Anthony (2004): An 8.5-carat blue diamond estimated at $4 million, adding to J.Lo’s collection of rare gems.
From Alex Rodriguez (2019): A 15–18 carat emerald-cut diamond valued at $1.8–$5 million.
In 2022, when Ben Affleck and Lopez rekindled their relationship and got engaged again, Affleck presented her with an 8.5-carat natural green diamond ring—her favorite color—making it one of the rarest and most personal celebrity engagement rings ever.
Hailey Bieber and Justin Bieber: Sleek and Sentimental
Justin Bieber proposed to model Hailey Baldwin in 2018 with a stunning oval-shaped diamond between 6 to 10 carats, designed by Solow & Co. The sleek, elongated diamond is set on a delicate gold band, balancing size with subtlety.
Later, Hailey paired it with a Tiffany & Co. diamond wedding band for a modern yet classic look. The ring mirrors their minimalist style and youthful sophistication.
Priyanka Chopra and Nick Jonas: Classic Elegance
Nick Jonas shut down a Tiffany & Co. store in London to select the perfect ring for Priyanka Chopra. The result? A cushion-cut diamond estimated at 5 carats, set in platinum with tapered baguette accents on either side.
Simple yet elegant, the ring is a timeless piece reflecting their cross-cultural fairy tale romance. Chopra’s reaction was tearful, and Jonas revealed that he waited until midnight on her birthday to pop the question.
Paris Hilton and Carter Reum: Diamonds Fit for a Heiress
In 2021, Paris Hilton got engaged to venture capitalist Carter Reum with a ring designed by Jean Dousset, great-great-grandson of famed jeweler Louis Cartier.
The ring featured a custom-cut 20-carat emerald-cut center diamond, flanked by trapezoid-shaped diamonds and surrounded by a halo. Hilton revealed that the design was inspired by the Grand Palais in Paris and called it “timeless elegance meets modern art.”
More Than Just a Ring
From royal palaces to red carpets, celebrity engagement rings aren’t just dazzling tokens of love—they are reflections of history, fashion, and deeply personal stories. Whether minimalist or maximalist, classic or cutting-edge, each ring carries layers of meaning, craftsmanship, and sentiment.
In a world obsessed with spectacle, it's heartening to remember that at the center of each stone is a story—a proposal, a promise, and a dream for forever.
