The Most Iconic Old Hollywood Engagement Rings

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Nothing screams glamour like Old Hollywood. Sound had only recently been introduced to movies, the film industry was booming, and silver screen stars dominated the pop culture conversation. Films of the period had a larger-than-life quality — dramatic acting, elaborate costumes, and expansive sets — and the visually rich style seeped into the lives of the era's icons like Marilyn Monroe and Elizabeth Taylor. The result was a zeitgeist full of dramatic fashions, feminine silhouettes, and a more-is-more approach to jewelry.

This produced an opulent diversion from real life during a period marked by the Great Depression, World War II, and the social upheaval of the 1960s.  Even now, it's not uncommon for modern celebrities to reference the era on the red carpet. "That kind of escapism and glamour is such an important part of why we resonate with this trend," historian Rachael Gibson told Vogue.

The stars of that time were prone to the same sort of romantic scandal as celebrities today. Dive into an Old Hollywood memoir, and you'll likely find whirlwind courtships, secret love affairs, and nasty divorces. Still, while love was a battlefield even then, there's no denying that the elegance of Old Hollywood made for some fabulous jewelry, particularly when it came to engagement rings.

Actor Elizabeth Taylor's relationship history is littered with red flags, as well as incredible diamonds. Taylor was married twice to fellow actor Richard Burton, and during their first marriage, he gifted her a 33.19-carat diamond ring set by Harry Winston. Originally named "The Krupp Diamond," the stone was subsequently renamed "The Elizabeth Taylor Diamond." "My ring gives me the strangest feeling for beauty," Taylor once said of the gem (via People). "It sort of hums with its own beatific life."

Elizabeth Taylor was married eight times and famously loved jewelry, so it's no surprise that the Hollywood icon has more than one memorable engagement ring on this list. A standout among them is the 29-carat emerald-cut diamond ring she received from movie producer Mike Todd. Taylor lovingly dubbed it her 'ice skating rink.' "She had such striking features that massive pieces of jewelry looked great on her," wrote one Reddit user. There are plenty of ways to bring Taylor's old Hollywood glamour to your outfits, but her massive rings are inimitable.

Though Lucille Ball initially wore a cheap brass ring to wed Desi Arnaz, he quickly upgraded her to a cushion-cut diamond ring that she reportedly selected herself. While the diamond and platinum ring stunned — and Arnaz also later gifted her an enormous 40-carat aquamarine ring — Ball cherished the original metal band. "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 wrote in her 1996 memoir "Love, Lucy" (via People).

Though Prince Rainier III initially proposed to actor Grace Kelly with an eternity band, the pair allegedly shopped together to select the baguette-flanked 10.48-carat diamond ring that became an iconic fixture on the star's left hand. "We have pictures of [the couple] peering in at the windows of the Cartier store on the Rue de la Paix [in Paris]," a representative from Cartier told InStyle, explaining that the pair likely were selecting her famous ring, worth a record-setting $4.6 million at the time.

In 1966, crooner Frank Sinatra proposed to actor Mia Farrow with a nine-carat pear-shaped diamond ring with diamond baguettes, which Farrow paired with a $27 frock for their wedding ceremony. Though the couple's marriage only lasted two years, the stunner of a ring has lingered much longer in cultural consciousness. "As a child I fell [in] love with the engagement ring given to Mia Farrow from Frank Sinatra and vowed that's what I would have one day," wrote one Reddit user.

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While plenty of Hollywood icons have sported enormous focal stones, actor Marilyn Monroe took a different tack when she married her second husband, baseball player Joe DiMaggio. Instead of an oversized rock, the ring was a low-profile platinum eternity band featuring 36 baguette-cut diamonds. Now, more than two and a half decades later, despite its unconventional style, the ring is considered iconic and continues to inspire countless imitations. "Absolutely gorgeous," wrote one Reddit user of the distinct but subtle style. "This is THE ring of all rings."

For her third marriage to movie producer Sid Luft, actor Judy Garland wore an enormous pear-shaped diamond on a platinum band. "When Sid said he had a little 'thing' for me and slipped the ring on my finger, I just cried. I really did," Garland told Modern Screen in 1954 (via InStyle). "Honestly, Sid's the most thoughtful guy!" The diamond was far more conventional than her previous ring — second husband Vincente Minnelli presented her with a pearl and onyx engagement ring — but the sheer size of the stone made it memorable.

Elizabeth Taylor's relationship with Richard Burton was so passionate that one monstrous diamond ring was hardly enough. Burton gifted Taylor another iconic ring, an enormous 69.42-carat pear-shaped diamond from Cartier, which would come to be known as the "Taylor-Burton Diamond." In fact, the diamond was so big that Taylor later had it fashioned into a pendant that she wore before eventually auctioning it off for charity. "I have never thought of my jewelry as trophies. I'm just here to take care of them," she explained (via Natural Diamonds).

Director Roman Polanski proposed to actor Sharon Tate with an extremely unusual ring: a large opal encircled in rubies. In fact, the ring was so unconventional that Tate herself was reportedly not a fan. "The ring was not Sharon's style and she never wore it," Tate's sister, Debra Tate, told TMZ in 2011. But the memorable piece reflected the '60s trend of selecting stones besides diamonds for engagement rings, though unlike the emeralds and sapphires that were also popular during the decade, opals were sometimes rumored to be bad luck.