15 Gorgeous Old Hollywood Celebrity Engagement Rings

Wallis Simpson

King Edward VIII gave American socialite Wallis Simpson a 19.77-karat emerald encircled by diamonds in a gold setting. The ring was engraved with the inscription: “We are ours now 27 x 36.”

The engraving was in honor of their secret engagement on Oct. 27, 1936 — six weeks before Edward officially abdicated. In 1987, the ring sold at auction for $1.98 million.

Lucille Ball

Though she joked around on her sitcom, I Love Lucy, Ball’s bling was no laughing matter. Desi Arnaz originally gave his wife a brass ring from Woolworth’s when they eloped in Greenwich, Conn., on Nov. 30, 1940 — about six months after meeting on the set of the musical comedy Too Many Girls earlier that year.

“Desi had planned to marry me at the office of Justice of the Peace John J.O’Brien. He had forgotten only one thing, a wedding ring,” Ball wrote in her 1996 memoir Love, Lucy, of their elopement. “Desi’s business manager ran into Woolworth’s and bought me a brass one.”

However, she later got a major upgrade: a cushion-cut diamond and platinum number.

“Although Desi later gave me a platinum ring, that little discolored brass ring rested among the diamonds and emeralds in my jewel case for years,” she added.

Lucille Ball

The Emmy Award-winning actress and comedian was also known to wear an enormous emerald-cut aquamarine on her left ring finger, rumored to have been given by Arnaz.

The sparkling stone matched her light blue eyes, and Nicole Kidman wore a lookalike piece while playing the star opposite Javier Bardem as Arnaz in the 2021 biopic Being the Ricardos.

Ball and Arnaz were together for two decades and welcomed two children: daughter Lucie Arnaz and son Desi Arnaz Jr., before divorcing in 1960.

Elizabeth Taylor

Hilton asked Taylor to marry him with a 4-carat diamond set in platinum. They said “I do” in 1950, when Taylor was 18, in a wedding paid for by MGM, according to British Vogue. The union lasted just eight months, with the pair divorcing in 1951.

Elizabeth Taylor

The Father of the Bride star headed to the altar again in 1952, after English actor Michael Wilding popped the question with a megawatt sapphire surrounded by diamonds. Taylor and Wilding had two sons together, Michael Jr. and Christopher, before divorcing in 1957. Wilding died in 1979.

Jackie Kennedy

The then-Massachusetts senator proposed to Jackie (née Jacqueline Bouvier) in June 1953 with a toi et moi ring designed by Van Cleef & Arpels. Per Vogue, the ring featured an interlocking 2.88-carat diamond and 2.84-carat emerald, both in emerald cuts, and a band comprised of baguette-cut emeralds and diamonds.

The couple wed in a lavish ceremony in Newport, R.I., in September of that year and remained together until JFK’s assassination on Nov. 22, 1963. They welcomed four children during their marriage — Arabella, Caroline, John F. Kennedy Jr. and Patrick — but only Caroline and JFK Jr. survived and left the hospital.

Marilyn Monroe

Whether or not diamonds are a girl’s best friend, Marilyn Monroe seemed pleased with the eternity band of 36 baguette-cut diamonds she wore as a wedding ring during her marriage to her second husband and Yankees baseball legend, Joe DiMaggio.

The couple tied the knot in January 1954 in DiMaggio’s native San Francisco and divorced nine months later in October. According to Vogue, it’s believed that Monroe was wearing a different ring during her courthouse wedding, but its origins and whereabouts are unknown.

Lana Turner

Hollywood’s Golden Age starlet Lana Turner might have gone through a divorce or seven; however, this pear-shaped showstopper from one of her eight husbands was a keeper.

Princess Margaret

In a romantic nod to Margaret’s middle name, Rose, Antony Armstrong-Jones presented his princess with a three-ruby ring, flanked by six smaller diamonds meant to mimic a rosebud, according to Brides. The couple wed three months after their 1960 engagement and later welcomed two children, son David Armstrong-Jones and daughter Lady Sarah Chatto, before divorcing in 1976.

Debbie Reynolds

Singin’ in the Rain actress Debbie Reynolds was starry-eyed beside Eddie Fisher at their 1954 engagement party, where she flashed her 7-carat, square-cut rock. All seemed well after they tied the knot in 1955, but their union dissolved in 1959.

Joan Crawford

Joan Crawford‘s fourth husband, Pepsi board chairman Alfred Steele, wowed her with an unusual double band of baguette diamonds — though it came after their 1955 wedding. The couple remained together until Steele’s death in 1959.

Grace Kelly

Though Prince Rainier III gave the American actress a $4.6 million, 10.47-carat, emerald-cut Cartier engagement ring for her to wear in the 1956 film High Society — her last movie before they wed — he first presented his bride-to-be with another piece of jewelry.

Initially, the Prince of Monaco proposed to Kelly with an eternity band featuring alternating rubies and diamonds, honoring the colors of the Monaco flag (via Brides). The royal couple announced their engagement in January 1956 and married four months later in April.

Elizabeth Taylor

Taylor sported a 29-carat diamond ring on her finger while she and Todd chatted with reporters before a flight to Mexico City in January 1957. The Raintree County star insisted that the emerald-cut treasure was a “friendship ring,” but the pair would tie the knot in Mexico on Feb. 2, 1957, just weeks after her divorce from Wilding was finalized.

The couple shared one daughter, Liza, and were together until Todd died in a plane crash just one year into their marriage in March 1958.

Mia Farrow

Mia Farrow received a 9-carat, pear-shaped sparkler set in platinum from her first husband, Frank Sinatra. The couple wed in 1966, two years after they started dating.

Sinatra purchased the ring from celebrity jeweler William Ruser, from whom he also bought a double-row diamond bracelet that he gave to the Rosemary’s Baby star as a wedding gift, according to Women’s Wear Daily. Their marriage was short-lived, with the pair finalizing their divorce in 1968.

Elizabeth Taylor

The “Queen of Diamonds” left Fisher for Burton, whom she first met at a Hollywood party in 1953 but fell for on set of 1963’s Cleopatra. They secretly wed in Montreal in March 1964 — just days after Taylor divorced Fisher.

Burton purchased a 33.19-carat, flawless gem for his wife in 1968. It was one of the many jewels he bought for her during their first marriage (which lasted 10 years) and second union of nearly a year.

The ring was originally referred to as the Krupp Diamond but is now called the Elizabeth Taylor Diamond.

“My ring gives me the strangest feeling for beauty,” she once said. “It sort of hums with its own beatific life.”