A man blessed with opportunity

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The view of the Hudson River from Sleepy Hollow Country Club. Photo: JH.

Friday, June 21, 2019. The first day of Summer 2019. It’s been raining off and on in New York for the past three days. Mainly a light, soft rain that washes the leaves and flowers and streets. And warm, but not too.

Next Thursday, June 27th, Doyle Galleries is holding an auction of the estate of Oleg Cassini at their galleries on 175 East 87th Street (between Lexington and Third). I tell you this because it’s an auction that would tempt me just out of (vulgar?) curiosity.

For example, on Saturday and Sunday and Monday, at The Moorelands, the 43 acre estate at 47 Sandy Hill Road in Oyster Bay Cove, there is a public viewing of the actual property as well as the items — more than 700 lots of furniture, silver, china, decorative objects, cars (now vintage Mercedes and an ’87 Rolls), as well as arms and armor, artwork, Continental and English silver memorabilia and items from the Gramercy Park townhouse.


A classic image of Cassini taken at the White House in 1962 with President Kennedy watching, amused by the designer’s posing for the camera. It occurred upon Mrs. Kennedy and Lee Radziwill’s return from their visit to India and Pakistan where the turban and monocle had been gifts. Estimate: $500 – $800.

Mr. Cassini died at 93 six years ago, a very rich man with an estate in the millions. He had a long career as a famous American fashion designer whose career — already long established at the time — took on the mantle of the designer who changed American fashion through his client Jacqueline Kennedy. 

He designed more than 300 outfits for the First Lady as well as her gown for the Inaugural Ball. More importantly, Jackie Kennedy had an enormous influence on American fashion. She was 31 and a perfect model. She already had taste and an eye, and she loved clothes, a marketer’s dream come true. A fashion designer’s dream come true also.


A group of approximately eight Oleg Cassini designed gowns and dresses., which includes a replica of the gown worn by Mrs. Kennedy at the gala reception for the president of Peru in September 1961 (pictured above). Of the original gown Cassini wrote “one of my favorite color combinations-jet black contrasted with vivid Tintoretto mustard-gold. The sleeveless tank top in jet silk was tied at the waist with the mustard-gold satin of the bell-shaped skirt with a signature bow fringed at the end.” Estimate: $1,000 – $2,000
Small photography archive with many images depicting Jacqueline Kennedy, Grace Kelly and others. Estimate: $100 – $200.
Two page autograph letter in blue signed “Jackie” to Oleg Cassini upon the death of his mother.
Estimate: $700 – $1,000.
Fine letter signed to Oleg Cassini in advance of the 1960 presidential election. Washington.
Estimate: $2,000 – $3,000.

At the time he was graced with this moment, Oleg Cassini was already an well-known American designer for women. It was no accident that Jackie Kennedy liked his ideas. The following is a description of his most famous silhouette designed for her in a first public appearance: “Meticulously tailored and featuring oversized buttons and boxy jackets, as well as occasionally dramatic décolletage.” 

In those days — in the cities and towns across America when I was growing up, Cassini was known as the once-husband of Gene Tierney, a beautiful movie star. His public image — designer-husband of a movie star) stuck with the fans. His family background, however, was far more worldly, however. So too, was his history – a child and man of his time.


Two notebooks of original fashion sketches. Estimate: $1,000 – $1,500.

He was born Oleg Aleksandrovich Loiewski in Paris in 1913, the elder son of  Count Alexander Loiewski, a Russian diplomat. His mother was Countess Marguerite Cassini, daughter of an Italian count who had been the Russian ambassador to the United States at the beginning of 20th century. 

In 1918, the Russian Revolution brought the fall of the Romanov monarchy. All of the elite, including the Loiewski family fled for their lives, leaving everything behind, including all property and wealth, escaping to Denmark, ending up in Florence, Italy. where they settled. The boys took the mother’s name – probably to make it easier politically and socially in their new country.


1987 Rolls Royce Silver Spur. Estimate: $8,000 – $12,000

Growing up among the European aristocracy, Oleg from youth was an excellent athlete, excelling at track, skiing, soccer, tennis and an accomplished equestrian. He was a jock, international style.

As a young boy he also like to draw. His mother, however, started a fashion house in Florence. At University he studied political science, but he also studied fine art under Giorgio de Chirico at the Accademia di Belle Arti Firenze; and then fashion with Jean Patou.


Group of five framed reproduction photographs of fashion designs made for Jacqueline Kennedy.
Estimate: $100 – $200.

In 1936, age 23, Oleg, with brother Igor traveled to New York. They’d come to America to seek their fortunes. Oleg later wrote he arrived with a tuxedo, two tennis rackets, a title and a talent. After winning a doubles tournament a the West Side Tennis Club, he learned that his partner was the head of Paramount Pictures and was looking for another designer. The next day Oleg started as “full designer” and moved to Hollywood.

What followed was an amazing life, fully lived. “My preoccupation is to make women look beautiful,” he told an interviewer in Time Magazine in 2005, the year before he died. He was a man blessed with opportunity that he was prepared for when it came his way.


Black and white portrait of Cassini, signed on the mat below the image “Avedon ’93”. Estimate: $200 – $300.

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