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Celebrity engagement rings have shaped bridal jewelry trends for decades, from Jackie Kennedy’s rule-breaking two-stone design in 1953 to Zendaya’s vintage-inspired cushion cut in 2025. Every great love story deserves a great ring, and these seven iconic rings prove that the most memorable ones are never just about the stone. They tell a story, set a trend and redefine what forever looks like.

Here’s a look at six of the most iconic celebrity engagement rings of all time, what makes each one special and what you can take away for your own ring journey.

Jackie Kennedy’s Toi Et Moi Ring (1953)

Image source: Getty Images

Jackie Kennedy’s engagement ring from JFK is widely considered the ring that launched the toi et moi trend. In 1953, JFK proposed with a Van Cleef & Arpels creation featuring a 2.88-carat diamond alongside a matching 2.84-carat emerald, both emerald-cut and set on a band accented with baguette diamonds and emeralds. The ring was reportedly worth over $1 million at the time.

The two-stone design was audacious for its era, when single-stone solitaires were the overwhelmingly standard choice. In 1962, as First Lady, Jackie sent it back to Van Cleef & Arpels to be redesigned, adding marquise-cut diamonds to frame the center stones with even more presence. Jackie’s ring started a trend for unique designs, with stars like Ariana Grande and Megan Fox later following in her footsteps with their own toi et moi choices.

Grace Kelly’s Emerald-Cut Cartier Diamond (1956)

Image source: Getty Images

Grace Kelly’s engagement ring from Prince Rainier III of Monaco is one of the most influential celebrity rings ever made, though the now-famous emerald-cut diamond was not the first ring he gave her. Prince Rainier originally proposed with a more modest ruby and diamond eternity band, crafted from heirloom family stones in the colors of the Monaco flag. 

Only a month later, he replaced it with a 10.48-carat emerald-cut diamond from Cartier, flanked by two tapered baguette stones set in platinum. The ring was so extraordinary that when Kelly filmed her final movie, High Society, in 1956, the production used the real ring on screen instead of a prop.

Kelly wore it for the rest of her life. The ring has since been credited with inspiring emerald-cut choices by Elizabeth Taylor, Beyoncé, Amal Clooney and dozens of other style icons. 

Penélope Cruz’s Sapphire Halo Ring (2009)

Penélope Cruz’s engagement ring from Javier Bardem is one of the most celebrated colored gemstone rings in celebrity history. Bardem proposed with a 3-carat oval blue sapphire set in a flower-shaped diamond halo. Not every iconic ring features a diamond, and Cruz’s ring is proof that color can be just as captivating.

Sapphires carry centuries of symbolism, including loyalty, wisdom and nobility. Blue sapphire engagement rings have held royal prestige since Princess Diana’s iconic ring, now worn by Kate, Princess of Wales. Cruz’s ring echoes that legacy while keeping things personal and intimate.

Deepika Padukone’s Rectangular Solitaire (2015)

Deepika Padukone’s engagement ring from Ranveer Singh is widely admired for its refined, minimalist elegance. Singh proposed in the Maldives in 2015, though the couple kept their engagement private for three years before their stunning 2018 Lake Como wedding. 

He later revealed that the ring cost far more than he could afford at the time, a testament to how much she meant to him. The three-month salary rule still gets tossed around, but 61% of people today agree it simply isn’t realistic. Proof that what makes a ring iconic was never the price tag. 

The ring is a sleek rectangular solitaire in platinum, a departure from the typical round brilliant cut and a reflection of Padukone’s understated sophistication. In Bollywood and beyond, her ring sparked real appreciation for emerald-cut and rectangular diamonds, cuts that prioritize clean lines and clarity over sparkle.

Ariana Grande’s Pearl and Diamond Ring (2020)

Image source: Instagram @arianagrande 

Ariana Grande’s engagement ring from Dalton Gomez stands out as one of the most sentimental celebrity rings in recent memory. Gomez worked closely with New York jeweler Jack Solow of Solow & Co. to create a toi et moi ring pairing a 5-carat oval-cut diamond set at a deliberate angle alongside a pearl with deep personal meaning.

Ariana’s grandmother had a ring made from a pearl from her late grandfather’s tie pin, with a note that it would protect her. Gomez made sure to honor that connection. The ring proves that the spirit of Jackie Kennedy’s 1953 design, two meaningful stones set side by side, never really went out of style.

Zendaya’s East-West Cushion Cut (2025)

Image source: Getty Images 

Zendaya’s engagement ring from Tom Holland is one of the most talked-about celebrity rings in recent years. It debuted at the 2025 Golden Globes and instantly set a new benchmark for vintage-modern style. The ring, designed by UK jeweler Jessica McCormack, features an approximately 5-carat cushion-cut diamond set east-west in a Georgian-inspired button-back style on a yellow gold band.

Tom Holland reportedly proposed over the 2024 holiday season at Zendaya’s family home. The cushion cut dates back to the 1700s, and the east-west horizontal setting gives that classic stone a strikingly modern attitude. It looks inherited rather than purchased, timeless without being predictable.

How To Find Your Own Iconic Engagement Ring

Every ring above is iconic not because of its price, but because of the intentionality behind it. Here are three things to carry into your own ring search.

• Prioritize meaning over trend: Ariana Grande’s pearl, Jackie Kennedy’s emerald and Deepika Padukone’s solitaire all prove the most memorable rings have a story. Incorporate a family stone, choose your partner’s birthstone or go fully custom to make it yours.
• Know your shapes: Oval cuts elongate and flatter. Cushion cuts feel vintage and romantic. Round brilliants maximize sparkle. Emerald and rectangular cuts offer sleek minimalism. Understanding which silhouette speaks to your style narrows things down fast.
• Make It Unmistakably Yours: From sapphires to pearls to two contrasting stones set side by side, the most iconic rings in history are the ones that feel completely personal. Let these celebrities inspire you to choose what feels wholly and unapologetically like you.

No matter your budget or style, the right ring is the one that carries meaning. Whether you draw inspiration from Jackie Kennedy’s rule-breaking two-stone design or Grace Kelly’s timeless emerald-cut elegance, let these legendary rings remind you that the most iconic choice is always a personal one. Start with what moves you, and the rest will follow.