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Harry Winston was relatively young when he began working at his father’s jewelry shop in New York. He developed a taste for fine jewelry at age 12 and purchased his first jewel at a pawn shop, a two-carat emerald. Three years later, he moved to Los Angeles to expand the family business. His first business primarily focused on diamonds and helped him launch Harry Winston Incorporated. In 1944, Winston made his debut in Hollywood when he lent diamonds to Jennifer Jones for the Oscars ceremony, who went on to win the award for Best Actress. The jewelry became a staple in Hollywood, and the pop culture phenomenon was further enhanced when Marilyn Monroe performed the song Diamonds Are A Girl's Best Friend.

The jewelry house has continued to acquire many notable diamonds through auctions and private purchases over the years, collecting different jewels with unparalleled clarity and shape. Let’s take a look at Harry Winston’s most expensive jewels.

Cascading Sapphire And Diamond Drop Necklace ($3.8 million)

 

Harry Winston introduced several designs with varied gemstones for its cascading drop necklace. One of the necklaces is a cushion-cut necklace adorned with sapphires in each direction and a matching set of earrings. Dame Helen Mirren was spotted wearing the stunning necklace during the 2018 Oscars night to match her pale blue Reema Acra gown.

Diamond Chandelier Earrings ($4.2 million)

 

A famous jewelry brand amongst celebrities, Harry Winston, introduced the trending chandelier earrings at the 2018 Academy Awards, and long-time collaborator Salma Hayek was spotted wearing the earrings. According to Harper’s Bazaar, her diamond ring and earrings were valued at $4.2 million, and the sparkling jewelry matched her shimmering purple Gucci dress, an Alessandro Michele creation.

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Diamond Lattice Bracelet ($4.5 million)

 

An ensemble worth millions, Harry Winston combined a cluster of its popular bracelets to create the ultimate cuff for any red carpet appearance. At the 2013 Oscars, Charlize Theron was spotted wearing the Harry Winston Platinum Cluster bracelet and the Lattice Bracelet, vintage jewels from the 1959 archives. Each weighed more than 50 carats and cost upwards of $3 million, while the matching earrings are valued at $1.6 million.

Golconda Diamond Necklace ($7.5 million)

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Golconda Diamond Necklace has a deep-rooted history that dates back to 2,000 years ago when a stunning 38-carat diamond was found in the Golconda region of India. Jacques Timey designed a necklace for the diamond, and Harry Winston had sold it to late heiress Christina Onassis, as noted by Robb Report. Unlike any other jewel, the diamond possesses an unmatched level of clarity, transparency, and purity.

Martian Pink Gold Ring ($17.4 million)

 

Harry Winston made its biggest round pink diamond sale in 2012 while selling the Martian Pink Ring for a whopping $17.4 million. The ring was named after The Viking Landers’ mission to Mars in 1976. With flawless clarity and D-color, the ring is settled between two 10-carat brilliant cut diamonds on an 18-carat gold band. The Harry Winston ring was sold to an unknown buyer from a private collector’s archive at Christie’s auction.

Heart of the Ocean Diamond Necklace ($20 million)

 

The Heart of the Ocean Diamond Necklace is famous for its impact on the world of jewelry and pop culture, as it was heavily featured in the iconic romance drama Titanic. The popularity of the necklace has grown over time due to the movie, and history dates back to Harry Winston, who designed the necklace with a 15-carat rare blue diamond. Actress Gloria Stuart wore the necklace at the 1998 Oscars ceremony, which was the most expensive jewel worn at an award show.

The Winston Blue Diamond Ring ($23.8 million)

 

The Harry Winston group made a flamboyant purchase in 2013 when it bought the largest vivid blue diamond in existence for $23.8 million. As mentioned by Forbes, the diamond was renamed The Winston Blue and weighed 13.22 carats, costing $1.8 million per carat. The diamond was purchased at a Christie’s Auction in Geneva at a public jewelry auction.

Winston Legacy Diamond ($26.7 million)

 

At the same ceremony, the brand made another hefty purchase with a 243-carat rough diamond. Discovered in Botswana at the De Beers mine, the gem was polished for 21 months before it was presented for the auction. After shelling out a whopping $26.7 million for the diamond, the group renamed it Winston Legacy to commemorate Harry Winston as the King of Diamonds.

Pink Legacy Diamond Ring ($50 million)

 

In 2018, Harry Winston made headlines again after making their biggest purchase at an auction when the team purchased a pink diamond for $50 million. Weighing a little below 19 carats, the diamond is valued at $2.6 million per carat, as stated by CNBC. The rectangular-cut diamond is mounted on a diamond band, and six bidders sought after the precious jewel. The diamond was eventually purchased via a representation of the Winston Group and renamed the Pink Legacy Diamond.

Harry Winston has continued to strive for excellence, and the jewelry brand has marked important milestones in its history with the purchase of extraordinary diamonds that are hard to attain. The legacy of its moniker continues to last in Hollywood through celebrities and its archival jewels.

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Sources: Harper’s Bazaar, Robb Report, Forbes, CNBC