The Best Celebrity Natural Diamond Engagement Rings of All Time

Mary of Burgundy, 1477

Archduke Maximilian of Austria became betrothed to Mary of Burgundy in 1477, proposing with a diamond engagement ring, before the tradition was the norm. It is considered to be the first diamond engagement ring proposal, kickstarting our best celebrity diamond engagement rings list. A letter written to Maximilian before he proposed reportedly read, “At the betrothal, your Grace must have a ring set with a diamond and also a gold ring.” In a portrait painted by Niklas Reiser, Mary is depicted wearing a solitaire on her right hand, which is often used to illustrate the point of her engagement ring, though there is no certain proof the ring in the painting is her engagement ring.

The ‘toi et moi’ engagement ring style can be traced back to an original natural diamond trendsetter Empress Joséphine. The French leader Napoleon Bonaparte proposed to his first wife in 1796 with a ‘toi et moi’ engagement ring featuring two pear-shaped stones – a sapphire and a diamond, positioned side-by-side to represent the meeting of two lovers. The engagement ring style has more recently been championed by the likes of Jackie Kennedy, Emily Ratajkowski, and Megan Fox.

Joséphine passed down her iconic engagement ring to her daughter, and for two centuries after, the the ‘toi et moi’ ring remained within the Bonaparte family. In 2013, the ring was sold off by French auction house, Osenat at the “L’empire à Fontainebleau, les rendez-vous de l’histoire” auction and fetched nearly $950,000.

Norma Shearer, 1927

As fancy shape diamonds skyrocketed in engagement rings during the Jazz Age, Hollywood starlet Norma Shearer championed the trend with one of the most recognizable fancy-cut diamond engagement rings of the era. In 1927, “The Boy Wonder of MGM,” producer Irving Thalberg proposed to Shearer in his office, The story goes that he offered up a tray filled with an assemblage of diamond engagement rings and told her to pick one.

The actress picked up a large marquise shape diamond set on a slender platinum band. According to The Adventurine‘s Marion Fasel, after Shearer received the ring, she wore it on-screen in all her films where she played a married woman, including 1939’s The Women.

Lucille Ball, 1940

Legendary Hollywood power couple Desi Arnaz and Lucille Ball of I Love Lucy fame eloped in 1940. At first, Arnaz gifted Ball a brass ring from Woolworth’s before upgrading her engagement ring to an impressive cushion-cut diamond and platinum ring.

Queen Elizabeth II, 1947

About five years before she ascended the throne to become the longest-reigning British monarch in history, Queen Elizabeth II announced her engagement to Prince Phillip in 1947 when she was still just a princess. The pair posed outside of Buckingham Palace to share the news, showing off her engagement ring with a three-carat round diamond center stone accompanied by 10 smaller pavé diamonds, including pieces from Prince Phillip’s mother, Princess Alice of Battenberg’s wedding day tiara.

Judy Garland, 1952

The Wizard of Oz actress Judy Garland married show business figure Sidney Luft in 1952. He proposed earlier that year with a large antique-cut pear shaped diamond solitaire engagement ring flanked by two tapered baguettes, set on a platinum band and paired with a thin diamond eternity wedding band.

Jackie Kennedy, 1953

Before he was President, then-Congressman John F. Kennedy proposed to Jacqueline Bouvier in 1953 with a toi et moi engagement ring from French jeweler Van Cleef & Arpels. The ring comprised of a 2.88-carat emerald-cut natural diamond alongside a 2.84-carat emerald-cut emerald on a band of baguette-cut diamonds and emeralds.

According to Vogue, her future father-in-law, Joseph Kennedy picked out the ring at the jeweler’s Fifth Avenue location in New York with the help of Hélène Arpels, who knew Jackie. About 10 years after the wedding, Jackie revamped the ring, replacing the baguette stones with a wreath of marquise-cut and round-cut diamonds.

Lana Turner, 1953

Lana Turner’s fourth out of seven husbands, actor Lex Barker proposed with an impressive pear-shaped natural diamond engagement ring. The pair was married from 1953 to 1957.

Debbie Reynolds, 1954

Singin’ in the Rain star Debbie Reynolds showed off her seven-carat square-cut natural diamond engagement ring from crooner Eddie Fisher at her 1954 engagement party.

Marilyn Monroe, 1954

In contrast to her quintessentially over-the-top bombshell glamour, Marilyn Monroe’s engagement ring from her second husband, baseball star Joe DiMaggio takes a more understated route. The platinum eternity band featured 36 baguette-cut diamonds and in 1999, the ring was sold at a Christie’s auction for a whopping $772,500. But there have been suspicions that Monroe was actually wearing a different ring during her courthouse wedding in 1954. According to the founder of the Marilyn Monroe collection, Scott Fortner, the original diamond engagement ring is believed to have been a DiMaggio family heirloom that was “used as a placeholder” for the hasty nuptials, yet not much is known about its origin story and where it is today remains a mystery. 

Joan Crawford, 1955

Academy Award-winning actress Joan Crawford married her fourth husband, Chairman of Pepsi-Cola, Alfred Steele in 1955. Allegedly, Steele forgot to purchase an engagement ring ahead of the wedding, so he quickly went for the wow factor with an unexpected double wrap band filled with baguette diamonds. 

Grace Kelly, 1955

While Prince Rainier III of Monaco originally proposed to American actress Grace Kelly over Christmas in 1955 at her family home in Pennsylvania with a Cartier diamond and ruby eternity band (with colors coordinating with Monaco’s flag), her second engagement ring from the royal is the one that has gone down in history. Just a month later, the Prince upgraded Kelly’s sparkler to a platinum Cartier ring with a 10.48-carat emerald-cut diamond, flanked by two baguettes. The iconic engagement ring even made an appearance in her 1956 film High Society.

Mia Farrow, 1966

Rosemary’s Baby actress Mia Farrow received a nine-carat, pear-shaped diamond engagement ring with a simple gold band from her first husband, “Ol’ Blue Eyes” Frank Sinatra, whom she married in 1966. The ring was purchased from renowned Beverly Hills jeweler, William Ruser.

Elizabeth Taylor, 1968

While her engagement rings from William Pawley Jr, Conrad Hilton, Michael Wilding, Mike Todd, and Eddie Fisher, all turned heads, it was Elizabeth Taylor’s engagement ring from Richard Burton that would demolish them all in comparison. Taylor and Burton’s decades-long love affair began in 1962 when the actors met on the set of their film Cleopatra. While Burton was known for adding the most exquisite diamonds to Taylor’s jewelry collection, the most iconic has to be the Elizabeth Taylor Diamond, previously known as the Krupp Diamond. Burton purchased the 33.19-carat Asscher-cut Type IIa diamond ring for Taylor in 1968. 

While the couple married twice — once in 1964 and again in 1975, the Elizabeth Taylor Diamond is not a ring Burton technically proposed with. Yet, Taylor was said to have worn it nearly every day. It was sold at a Christie’s auction in December 2011 for $8.8 million, according to Forbes.

Carolyn Bessette-Kennedy, 1995

John F. Kennedy proposed to fashion publicist Carolyn Bessette-Kennedy in 1995 with a minimalist engagement ring inspired by his mother Jackie Kennedy’s “swimming ring.” The platinum eternity band featured round-cut sapphires and diamonds. 

Sarah Jessica Parker, 1997

Sarah Jessica Parker tied the knot with fellow actor Matthew Broderick in 1997. The Sex and the City alum’s large emerald-cut natural diamond engagement ring is estimated to weigh from seven to eight carats on a yellow gold band— arguably even more dazzling than her iconic character Carrie Bradshaw’s engagement rings from both Aiden Shaw and Mr. Big.

Victoria Beckham, 1998

Soccer legend David Beckham popped the question and proposed to the Spice Girls alum back in 1998. The couple announced their engagement with a press conference that January outside a Cheshire, England hotel, where Victoria showed off her marquise-cut diamond, set with a yellow gold band to photographers. Ever since, the pop star-turned-fashion designer has added over a dozen engagement rings to her collection of sparklers. 

Heidi Klum, 2004

British musician Seal proposed to German supermodel Heidi Klum over the holidays in 2004 with a 10-carat canary yellow oval-shaped diamond engagement ring, set with a thin pavé-set yellow diamond band, courtesy of renowned celebrity jeweler Lorraine Schwartz.

Anna Kournikova, 2004

Russian tennis star Anna Kournikova first revealed her gigantic pink diamond during the 2004 World Team Tennis game from musician Enrique Iglesias, stirring engagement rumors though the long-time couple never confirmed or denied if they were officially engaged. The 11-carat pear-shaped Argyle natural pink diamond is anchored by two trillion-cut white diamonds on either side.

Beyoncé, 2007

In the words of Beyoncé Giselle Knowles-Carter, “If you liked it then you should have put a ring on it.” And Jay-Z most certainly did. The rapper proposed to Beyoncé with an enormous emerald-cut diamond engagement ring, set in a micro pave split shank band, designed by Lorraine Schwartz. The diamond is estimated to weigh between 18 and 24 carats, and worth about $5 million. 

Mariah Carey, 2008

Nick Cannon proposed to Mariah Carey in 2008 with an emerald-cut fancy light pink diamond engagement ring, surrounded by 58 intense pink diamonds and flanked by two half-moon diamonds from Jacob & Co. jewelers. At the time, Cannon told People, “We got the pinkest stone we could find, surrounded by other diamonds.”

Jessica Biel, 2012

Pop star Justin Timberlake proposed to actress Jessica Biel over the holidays in 2011 with a square-cut diamond engagement ring, replete with two pavé halos and aquamarine embellishments (Biel’s birthstone) on either side of the center diamond. 

Angelina Jolie, 2012

Seven years into their relationship, Angelina Jolie and Brad Pitt made it official in 2012, with Jolie debuting a multi-stone engagement ring with a stunning emerald cut diamond at its center to mark the milestone. The one-of-a-kind design was created in collaboration between Pitt and Beverly Hills jeweler Robert Procop. At the time, the designer told The Hollywood Reporter, “I was able to locate a diamond of the finest quality and cut it to an exact custom size and shape to suit Angelina’s hand.” Procop elaborated, “Brad was always heavily involved, overseeing every aspect of the creative design evolution. The side diamonds are specially cut to encircle her finger. Each diamond is of the highest gem quality.” The couple lovingly referred to as “Brangelina” married in 2014 and later filed for divorce in 2016. 

Kim Kardashian, 2013

As I’m sure we all remember, Kim Kardashian’s third husband, rapper Kanye West rented out AT&T Park in San Francisco in 2013 for his iconic proposal to the reality television star. He popped the question with a perfect D flawless type 2A cushion-cut diamond, weighing in at 15 carats with a thin pavé band, designed by Lorraine Schwartz. In 2016, the engagement ring was stolen from Kardashian when robbers broke into her Paris hotel room – the ring was never recovered.

Gabrielle Union, 2013

Basketball legend Dwyane Wade proposed to actress Gabrielle Union in 2013 with an 8.5-carat cushion-cut engagement ring, crafted by jeweler Jason of Beverly Hills. Union shared with Only Natural Diamonds that, at the time, “They started writing little op-eds about it and estimating what the cost might be, and I became terrified to wear it in public without a full armed security detail.”

Mary-Kate Olsen, 2014

One-half of the beloved twin-acting duo-turned-acclaimed founders of fashion label The Row, Mary-Kate Olsen married Oliver Sarkozy in 2015 before ultimately splitting in 2020. The French banker proposed to the former child star in 2014 with a vintage 1953 Cartier diamond engagement ring acquired from Sotheby’s Auction House. With a four-carat European-cut diamond at the center, the stone is set inside a halo of 16 sapphires and petals of single-cut diamonds in a gold setting. The ring sold for $81,250. 

After years as Hollywood’s favorite bachelor, actor George Clooney proposed to human-rights attorney Amal Alamuddin in April of 2014 with a swoon-worthy ethically mined seven-carat emerald-cut diamond engagement ring, with two tapered baguettes on each side, set in platinum. 

Jennifer Aniston, 2015

Friends icon Jennifer Aniston became engaged to fellow actor Justin Theroux in 2012 when she began wearing a massive solitaire diamond. “It’s a rock, I know,” she told the New York Times. “He rocked it up. It took me a while to get used to it.” The couple tied the knot in 2015 before splitting in 2018.

Serena Williams, 2016

Tennis legend Serena Williams said “yes” to Reddit co-founder Alexis Ohanian in December 2016, debuting a mega-carat diamond engagement ring that’s estimated to have cost $3 million.  

Ciara, 2016

Ciara slipped an enormous 16-carat diamond engagement ring on her left ring finger in 2016 when she became engaged to NFL player Russell Wilson. Surrounded by four diamonds on both sides, the songstress tends to wear the stunner in between two eternity bands.

Meghan Markle, 2017

Prince Harry popped the question to Meghan Markle in November of 2017 with a 3-carat cushion-cut natural diamond engagement ring flanked by two smaller side diamonds on a yellow gold band. The center stone was ethically sourced from Botswana while the two side diamonds originally belonged to Harry’s late mother, Princess Diana. About a year into their marriage in 2019, Harry updated the ring with a thin micro-pavé eternity band.

Cardi B, 2017

In 2017, Migos rapper Offset proposed to Cardi B onstage during a performance in Philadelphia with a whopping eight-carat pear-shaped diamond engagement ring encircled in two halos of about three more carats of diamonds and pink gems with two baguettes on either side. The stunner is reportedly worth $500,000.

Hailey Bieber, 2018

In 2018, pop star Justin Bieber popped the question to Hailey Baldwin while the couple was vacationing in the Bahamas. The one-of-a-kind engagement ring featured a giant oval diamond, which boasts between 6 to 10 carats and was custom-designed by Jack Solow of NYC-based jeweler Solow & Co. with Justin’s input. “Justin gave this a lot of thought,” Solow told People. “When I saw him, I think he was very happy about what we did together.” Since their wedding ceremony in 2019, Mrs. Bieber has been known to wear her ring with two wedding bands — a diamond and gold Soleste V ring and a band ring, both from Tiffany & Co.  

Emily Ratajkowski, 2018

In 2018, model, author, actress, and Inamorata founder Emily Ratajkowski married Sebastian Bear-McClard in a surprise ceremony at City Hall in New York City. At the time, the couple wore simple wedding bands they made together out of melted gold. Ratajkowski revealed that Bear-McClard didn’t have an engagement ring at the time of the proposal, so he offered a paper clip in the meantime. 

About four months after the nuptials, Ratajkowski showed off her upgraded engagement ring – a massive diamond toi et moi ring, featuring a square-cut diamond next to a pear-cut diamond on a gold band, designed by the couple and Ratajkowski’s friend, Alison Lou jewelry designer Alison Chemla, , landing her on our list for the best celebrity diamond engagement rings of all time.

Rooney Mara, 2019

Actress Rooney Mara became engaged to Joaquin Phoenix in May 2019, when she became one of the first high-profile celebrities to wear a hexagon-shaped portrait-cut diamond engagement ring with two slender tapered baguettes, fitting perfectly with her perennially unique style choices.

Scarlett Johansson, 2019

In 2019, actress Scarlett Johnson debuted her rare 11-carat elongated oval type 2A light brown diamond engagement ring mounted on a black ceramic curved band from her now-husband, Saturday Night Live comedian Colin Jost. The outstanding sparkler comes courtesy of Taffin jewelry designer James de Givenchy. 

Nicola Peltz-Beckham, 2020

Brooklyn Beckham, the eldest son of soccer star David Beckham and Spice Girl-turned-fashion designer Victoria Beckham proposed to his now-wife Nicola Peltz Beckham in 2020 with an emerald-cut diamond ring. Clearly taking a note from her mother-in-law’s expansive engagement ring collection, Nicola updated to a large oval-cut diamond with an eternity band encrusted with emerald-cut diamonds ahead of their wedding in 2022. 

Lily Collins, 2020

Lily Collins announced her engagement to director Charlie McDowell in September 2020. McDowell popped the question in New Mexico with a ring that is believed to feature a 3-carat cushion-shaped, rose-cut, center stone on a flared, yellow-gold textured bezel that allows one to see through the diamond. McDowell helped design the one-of-a-kind bauble with renowned jeweler Irene Neuwirth. “Thank you for making the most beautiful ring I’ve ever seen,” McDowell wrote to Neuwirth on Instagram. Collins commented, “Thank you from the bottom of my heart SO much for the most stunning, perfect ring. It’s breathtaking.”

Kate Hudson, 2021

Kate Hudson confirmed her engagement to Danny Fujikawa at the 2021 Met Gala red carpet where she debuted her elongated cushion cut light brown diamond engagement ring with a rose gold band from Lorraine Schwartz.

Paris Hilton, 2021

Carter Reum proposed to Paris Hilton during her 40^th birthday celebrations with a whopping emerald-cut diamond estimated to be between 10 to 15 carats. The custom diamond ring was designed by the great-great-grandson of French jeweler Louis Cartier, a jeweler in his own right, Jean Dousset. The Atelier even decided to name the design “Paris” after her.

Kourtney Kardashian, 2021

Blink-182 drummer Travis Barker proposed to reality television star Kourtney Kardashian beachside in Montecito, California with a large oval shape brilliant cut diamond engagement ring, designed by Lorraine Schwartz, estimated to weigh in at about 10 carats, priced at $500,000. In 2022, the couple tied the knot three separate times: once in Las Vegas, next at a Santa Barbara courthouse, and again in a lavish ceremony in Portofino, Italy. 

Jennifer Lopez, 2022

After Ben Affleck popped the question to Jennifer Lopez with a 6.1-carat Harry Winston pink diamond back in 2002, the actor chose another colorful diamond this time around. 20 years later, Affleck proposed in 2022 with an 8.5-carat cushion cut fancy vivid green diamond engagement ring, symbolizing “luck,” according to Lopez, who has said green is her lucky color. Purchased from Ilan Portugali of Beverly Hills Diamonds and designed by Rahaminov, the stone is set in a classic platinum mounting with a trapezoid-shaped white diamond on each side.

Megan Fox, 2022

Self-proclaimed “twin flames,” Machine Gun Kelly and actress Megan Fox made it official in 2022 with a toi et moi diamond and emerald ring from Stephen Webster. The musician popped the question with both pear shaped gems on January 11 under a Banyan tree in Puerto Rico.“It’s a thoroughbred Colombian emerald, with no treatment. It was just carved into the teardrop, straight out of the mine,” the rapper told Vogue. “The concept is that the ring can come apart to make two rings. When it’s together, it’s held in place by a magnet. So you see how it snaps together? And then it forms an obscure heart. And you see this right here? The bands are actually thorns. So if she tries to take it off, it hurts.”

Sofia Richie, 2022

Sofia Richie announced her engagement to music executive Elliot Grainge in April 2022. Her emerald-cut diamond sits on a plain platinum band for ultimate sparkle. Richie Grainge added more sparkle to her stack with an eternity wedding band made from a special collection of Asscher cut diamonds set in platinum as well as a 3 sided mircoset diamond eternity band, both from Martin Katz.

Ashley Benson, 2023

Pretty Little Liars star Ashley Benson announced her engagement to oil heir Brandon Davis on Instagram over the summer, bringing our best celebrity diamond engagement rings list into 2023. Our experts believe that her oval brilliant-cut diamond weighs at least 10 carats and is worth approximately $1M. 

Demi Lovato, 2023

Musician Jutes proposed to songstress Demi Lovato with a custom ring from Material Good, featuring a natural pear-shaped diamond set on a modern gold band, landing the singer on our best celebrity diamond engagement rings list. The diamond looks to be approximately 7 carats, and with high color and clarity it would be worth about $300K.

Zoë Kravitz, 2023

Zoë Kravitz and Channing Tatum were first spotted at a Halloween party dressed as characters from Rosemary’s Baby, with Kravitz sporting a sizable diamond ring on her left hand. Our experts think the ring is likely by British designer Jessica McCormack, as Kravitz has been known to wear her jewelry in the past. “I live in her jewelry, I really do,” Kravitz once said about McCormack. “I love that Jessica creates these special, unique pieces that look great with a gown, but also a t-shirt. That’s totally my vibe.”