Old Hollywood Engagement Rings

Grace Kelly wedding ring

Over the years, the Old Hollywood era of the late 1920s – early 1960s has become associated with elegance, glamor, and drama. This goes for both the films of the period and the lives of the performers who starred in them. The history of engagement rings and wedding rings stars have sported are no exception.

The famous actresses of classic Hollywood wore wedding bands and engagement rings that were both unique and extravagant. The following is a list of some of the most stunning Old Hollywood engagement rings.

Norma Shearer

Norma Shearer engagement ring

One of the first Hollywood movie starlets, Norma Shearer married “Boy Wonder” MGM executive Irving Thalberg in 1927. After a long off-and-on courtship, Thalberg proposed to Shearer in true Hollywood fashion. The story goes that he called his future wife into his office at MGM and presented her with a tray full of diamond engagement rings. He then let her choose whichever ring she wanted. Shearer chose the massive marquise cut engagement ring pictured above.

Grace Kelly

Princess Grace's emerald cut engagement ring. Photo: InStyle
Princess Grace wearing her engagement ring. Photo credit: InStyle.

In January 1956, Prince Rainier III of Monaco proposed to Grace Kelly with what turned out to be one of the most iconic emerald cut engagement rings in history. Princess Grace’s 10.47-carat sparkler is set in platinum with a baguette diamond on either side. She famously wore it anywhere and everywhere, including in her last screen performance as Tracy Lord in High Society.

You can find similar emerald cut engagement rings here and here.

Audrey Hepburn

Elfin beauty Audrey Hepburn was married twice, but her pair of wedding rings from first husband Mel Ferrer are especially noteworthy. Known as a trendsetter and fashion enthusiast, it is only fitting that Ferrer gifted Hepburn two different rings when they were wed in September 1954.

The ring set consisted of a pair of stackable wedding bands. One was rose gold and one was white gold, so Hepburn could choose to wear one or both depending on her outfit and mood on a given day. Once again, Audrey Hepburn revealed herself as truly ahead of her time; she adopted the stackable rings trend decades before the general public.

Marilyn Monroe

Marilyn Monroe eternity band

If you don’t count her rumored dalliance with a certain Mr. President, Marilyn Monroe’s marriage to baseball legend Joe DiMaggio was undoubtedly her most famous relationship. The two eloped in 1954 at San Francisco’s City Hall and were married for just nine months, but they remained friends for the rest of their lives.

Monroe’s wedding ring from her marriage to DiMaggio was a platinum eternity band lined with thirty-six baguette diamonds. As it turns out, the wedding band has had a much longer life than the marriage. In 1999, it sold at a Christie’s auction for $772,500.

In 2011, there was a great deal of hype surrounding Marilyn Monroe’s wedding ring again as it was rumored to be part of another high value auction. The ring lost one of its baguette diamonds in the twelve years that passed between auctions, so it was set at a much lower value. Despite all the media coverage Monroe’s eternity band was getting in 2011, though, the ring never went to its second auction.

You can find similar eternity bands here and here.

Lauren Bacall

Lauren Bacall wedding ring

Lauren Bacall and Humphrey Bogart’s marriage lives on as one of the most famous love affairs in Hollywood history. They were married on a farm in Ohio in 1945, and their May-December romance lasted until Bogart’s death in 1957. Lauren Bacall’s wedding ring is a bit of a mystery, but it appears to have a colored gemstone in the center and a relatively thick band width.

Elizabeth Taylor

With a grand total of eight marriages and seven husbands, it’s no surprise that Elizabeth Taylor built up an impressive jewelry collection throughout the course of her life. We chose the wedding jewelry from her first three marriages, for two reasons. Her first three marriages occurred during the heyday of Old Hollywood, and the engagement and wedding jewelry from these marriages represent three distinct ring styles.

Though her first marriage to Conrad Hilton ended messily after only eight months, it began with a gorgeous engagement ring. Hilton proposed to Taylor with a 4-carat diamond set in platinum (which you can see here). She and the hotel heir had a rocky relationship, but there’s no denying the simple elegance of her first engagement ring.

Elizabeth Taylor sapphire engagement ring

Taylor remarried just three months after leaving her volatile marriage to Conrad Hilton. Her second husband was English actor Michael Wilding, who fathered Taylor’s two eldest children. Forever known for her standout signature style, Elizabeth Taylor was a trendsetter with her second engagement ring. During her second marriage, she wore a domed sapphire ring that was completely outside of the norm for the time. With this unique style choice, Elizabeth Taylor set a trend for sapphire engagement rings.

You can find similar sapphire styles here and here.

Following her divorce from Wilding, Liz Taylor again wasted no time before remarrying. In 1957, producer and entrepreneur Mike Todd became Taylor’s third husband. Perhaps Mike Todd was following the buzz surrounding the wedding of Grace Kelly and the Prince of Monaco, because for her third marriage Liz Taylor received an emerald cut engagement ring. Liz’s ring, however, was almost three times the size of Princess Grace’s. At a massive 29.47 carats, the ring surely turned heads.

You can find similar styles here and here.

Judy Garland

Judy's Garland's engagement ring
Judy Garland’s engagement ring.

Judy Garland’s engagement ring from Vincente Minnelli (yes, Liza’s father) was truly one of a kind. Ahead of their wedding in 1945, Minnelli gifted Garland a pink pearl engagement ring set in black onyx. There are notoriously few photos of this ring out there. As you can see, even the best picture we found doesn’t do any justice to the ring’s detail. A pearl and onyx ring is quite an offbeat piece even in today’s time, so it was an incredibly unusual wedding jewelry choice in the 1940s. This should come as no surprise, given Garland’s notoriously eccentric personality.

The engagement and wedding rings of Old Hollywood were just as stylish and unique as the stars that wore them. What’s your favorite Old Hollywood engagement ring? Do you have a ring with a similar style to these starlets? Share your favorites, photos, and questions in the comments below!