From Elizabeth Taylor’s legendary diamonds to Jackie Kennedy’s unique toi et moi, Old Hollywood engagement rings were more than just jewelry—they were symbols of enduring glamour, dramatic love stories, and timeless style that continue to inspire future brides and fascinate fans across generations.
Old Hollywood stars were masters of glamour, and their engagement rings were no exception. These iconic pieces, sported by screen sirens and style legends like Elizabeth Taylor and Jackie Kennedy, continue to dazzle and inspire today, proving that true elegance is timeless. Featuring both classic and unique designs, nearly all of these vintage treasures shared one major thing in common: spectacular diamonds, often paired with other precious stones. These rings are not just historical artifacts; they are enduring symbols of love, status, and the unparalleled allure of a bygone era.
Elizabeth Taylor: The Queen of Diamonds and Devotion
No discussion of iconic engagement rings would be complete without Elizabeth Taylor. Famously engaged ten times and married to seven different men in eight weddings, Taylor’s collection of sparklers was as legendary as she was. Her rings from Conrad “Nicky” Hilton Jr., Michael Wilding, Mike Todd, and Richard Burton (whom she married twice) are still celebrated for their sheer beauty and dramatic scale.
Early Engagements: From Classic Diamond to Sapphire
Taylor’s first engagement to Conrad Hilton Jr. in 1950, when she was just 18, featured a stunning 4-carat diamond set in platinum. This classic choice began her journey into the world of extraordinary jewelry. Following her divorce, she walked down the aisle again in 1952 with English actor Michael Wilding, who proposed with a striking sapphire ring encircled by diamonds. These early pieces set the tone for her future, demonstrating her evolving taste and love for precious gemstones.
The ‘Friendship Ring’ and the Legendary Krupp Diamond
Her third husband, Mike Todd, presented her with a spectacular 29-carat emerald-cut diamond in 1957, which Taylor playfully insisted was a “friendship ring” before their wedding. Tragically, their marriage was cut short by Todd’s death in a plane crash a year later. Years later, her relationship with Richard Burton led to one of the most famous jewels in history. In 1968, Burton purchased a 33.19-carat flawless gem, initially known as the Krupp Diamond, which became the illustrious Elizabeth Taylor Diamond. Taylor herself described its beauty, stating, “My ring gives me the strangest feeling for beauty. It sort of hums with its own beatific life,” as noted by People. This diamond remains a benchmark for celebrity engagement rings.
Jackie Kennedy’s Iconic Toi et Moi
A symbol of timeless sophistication, Jackie Kennedy’s engagement ring from John F. Kennedy was a true masterpiece of design. Proposed in June 1953, the ring was a unique toi et moi design by Van Cleef & Arpels. As reported by Vogue, it featured an interlocking 2.88-carat diamond and a 2.84-carat emerald, both emerald cuts, complemented by a band adorned with baguette-cut emeralds and diamonds. This distinctive style, featuring two different stones, represented the couple’s intertwined destinies and showcased a refined French influence that resonated with Jackie’s elegant personal style.
Royal Sparkle: Wallis Simpson and Princess Margaret
The allure of Old Hollywood’s engagement rings extended to royalty, blurring the lines between celebrity and monarchy. Wallis Simpson, the American socialite for whom King Edward VIII abdicated the throne, received an extraordinary 19.77-karat emerald encircled by diamonds in a gold setting. The ring was famously engraved with “We are ours now 27 x 36,” commemorating their secret engagement date on October 27, 1936. This ring sold at auction for an astonishing $1.98 million in 1987, underscoring its historical and material value.
Similarly, Princess Margaret’s engagement ring from Antony Armstrong-Jones was a romantic and personal design. In a nod to her middle name, Rose, the ring featured three rubies flanked by six smaller diamonds, crafted to resemble a rosebud, according to Brides. These royal engagements highlighted how even the most traditional figures embraced unique and meaningful designs in their symbols of commitment.
Grace Kelly: Two Rings Fit for a Princess
The fairytale engagement of Hollywood actress Grace Kelly to Prince Rainier III of Monaco involved not one, but two significant rings. Initially, Prince Rainier proposed with an eternity band featuring alternating rubies and diamonds, a thoughtful tribute to the colors of the Monaco flag. However, for her final film, 1956’s High Society, Kelly wore a more extravagant 10.47-carat emerald-cut Cartier diamond ring, valued at $4.6 million, which became her primary engagement ring and is now one of the most famous royal jewels.
Unique Stories and Stunning Designs
Beyond the royalty and multi-married legends, other Old Hollywood figures contributed to the era’s dazzling legacy of engagement rings:
- Lucille Ball: While Desi Arnaz initially gave her a brass ring from Woolworth’s when they eloped in 1940, Ball later received a substantial upgrade: a cushion-cut diamond and platinum ring. She was also known to wear an enormous emerald-cut aquamarine that matched her distinctive light blue eyes.
- Marilyn Monroe: Though her short marriage to Joe DiMaggio lasted only nine months in 1954, Monroe sported an eternity band of 36 baguette-cut diamonds as a wedding ring. The origins of her engagement ring worn at their courthouse wedding remain unknown, according to Vogue.
- Lana Turner: Known for her many marriages, Turner’s pear-shaped diamond from one of her eight husbands was a true showstopper and a testament to her glamorous persona.
- Debbie Reynolds: The Singin’ in the Rain actress received a magnificent 7-carat, square-cut diamond from Eddie Fisher at their 1954 engagement party.
- Joan Crawford: Her fourth husband, Pepsi board chairman Alfred Steele, presented her with an unusual double band of baguette diamonds after their 1955 wedding.
- Mia Farrow: Her first husband, Frank Sinatra, proposed with a 9-carat, pear-shaped diamond set in platinum in 1966. Sinatra purchased the ring from celebrity jeweler William Ruser, as reported by Women’s Wear Daily.
The Enduring Appeal of Vintage Glamour
The engagement rings of Old Hollywood celebrities remain a powerful source of inspiration. Their designs, whether a classic diamond solitaire or an avant-garde combination of stones, transcend fleeting trends. These rings offer a glimpse into the personal stories and grand romances of an era defined by unparalleled star power. For modern brides-to-be seeking something truly special, the influence of these vintage treasures is undeniable, as they continue to shape ideas of beauty, luxury, and lasting love.
