Diamonds Fit for Royalty: The 5 Most Expensive Harry Winston Rings Ever Auctioned

A Brief History of Harry Winston

Harry Winston, known as the “King of Diamonds,” was born in New York City and started in the jewelry industry at a young age, working for his father’s jewelry company. Winston opened his first store on Fifth Avenue in 1920, called “Premier Diamond Company.” Soon after, Winston quickly became a gemstone connoisseur, making a name for himself by recutting gems he found in estate sales.

His specialty was finding outdated jewelry at low prices and recutting them to enhance their sparkle and give them a modern look. His signature pieces caught the attention of many socialites, Hollywood stars, and collectors of the time. In 1947, Harry Winston was crowned the “King of Diamonds” by Cosmopolitan magazine. Today, his pieces are among the most sought-after collectibles in the high-end jewelry market.


Harry Winston Rings

While all Harry Winston pieces are respected with reverence, his rings stand out as the most distinguished works of the famous luxury company. As one of the biggest names in special jewelry, particularly diamonds, every ring created by Harry Winston is a masterpiece. Many celebrities have worn Harry Winston diamond rings.

Most notably, Elizabeth Taylor, Marilyn Monroe, Nicole Kidman, and Jennifer Lopez have all worn Harry Winston rings. In recent years, many Harry Winston rings have sold for record-breaking prices at Sotheby’s auctions.


The Five Most Expensive Harry Winston Rings


TOP 1

Harry Winston Light Pink Diamond Ring, Valued at $14 Million

Harry Winston Light Pink Diamond Ring, Valued at $14 Million
A magnificent light pink diamond ring, Harry Winston, circa 1970.

In 2017, this 33.36-carat fancy light pink diamond sold for 12.6 million Swiss francs (approximately $14 million). At this auction, it set a world record for the highest-selling fancy light pink diamond at auction. Fancy light pink diamonds are extremely rare.

Additionally, the perfect cut and near-flawless clarity added to the value of this ring. This unique gem was set by Harry Winston in 1970; the diamond is a step-cut light pink diamond with VVS1 clarity. This ring represents the craftsmanship and superiority of Harry Winston diamonds.


TOP 2

Harry Winston Diamond Ring, $3.7 Million

Harry Winston Diamond Ring, $3.7 Million
A Harry Winston pear-shaped diamond ring.

This unique pear-shaped diamond ring sold for 3.3 million Swiss francs (approximately $3.7 million) at a Sotheby’s auction. The pear-shaped diamond weighs 32.42 carats, is D color, and has VVS1 clarity. This diamond has almost no internal flaws, which is extremely rare for a diamond of this size. A 32.42-carat diamond is about the size of a cherry tomato. The center diamond is set between two tapered baguette diamond shoulders.


TOP 3

Harry Winston Cushion-Cut Sapphire Diamond Ring, $2.5 Million

Harry Winston Cushion-Cut Sapphire Diamond Ring, $2.5 Million
A cushion-cut sapphire ring.

This Harry Winston sapphire ring sold for 19.8 million Hong Kong dollars (approximately $2.5 million) at a Sotheby’s auction in Hong Kong. The ring features a 16.65-carat cushion-cut sapphire. This blue sapphire is flanked by two triangular diamonds, set in 18k gold. In the SSEF report, it states that the sapphire originates from Kashmir.

Kashmir sapphires are highly sought after, known for having the deepest royal blue color. This Harry Winston sapphire ring is no exception, with the sapphire being a rich, velvety blue color. Furthermore, this is an outstanding size and weight for a sapphire from this region of the world.


TOP 3

Harry Winston Diamond Ring, $2.1 Million

Harry Winston Diamond Ring, $2.1 Million
A cushion modified brilliant-cut diamond ring.

This Harry Winston cushion-shaped ring, set with a modified brilliant-cut diamond, sold for 1.8 million Swiss francs (approximately $2.1 million) at Sotheby’s Magnificent and Noble Jewels auction. The simple setting and iconic jeweler’s cut embody timeless beauty.

This cushion-cut diamond weighs 51.52 carats. Two shield-shaped diamonds on either side of the center diamond enhance its effect. The impressive size of this diamond makes it stand out, and additionally, this diamond is F color and internally flawless.


TOP 5

Harry Winston Diamond Ring, $1.4 Million

A pear-shaped diamond ring.
A pear-shaped diamond ring.

This incredible pear-shaped diamond ring sold for $1.4 million at a Sotheby’s auction. This diamond ring weighs 23.65 carats and is flanked by two tapered baguette diamonds. The diamond is D color with VVS2 clarity.

This diamond ring comes from the collection of Mr. and Mrs. Richard “Red” Skeleton. Red Skeleton was considered one of the most talented comedians of the 21st century. Unknown to the public, he was also an avid jewelry collector who privately enjoyed wearing diamond rings. This Harry Winston diamond ring was one of the most expensive pieces in his entire collection.

Diamonds Fit for Royalty: The 5 Most Expensive Harry Winston Rings Ever Auctioned