Most Leasiders know that 2024 marks the 100th anniversary of Bessborough public school. What they may not know is that the school counts among its alumnae one of the world’s most celebrated fashion models of the 1950s. Her name was Isobel Benn (1929-2012) and her story is one of remarkable success and accomplishment.
Young Isobel lived in Leaside with her family at 22 Cameron Cresc. from 1933 to 1936 and again from 1940 to 1944. (The family resided briefly in East York in the late 1930s.)
In the early 1940s, Isobel attended Bessborough school where she proved herself a high achiever. In November 1941, at age 12, she was selected over 11 other contestants as the primary-school champion orator of York County for her speech “V for Victory” – receiving a $25 war bond for her effort. A month later came an invitation to speak at the Leaside Lions Club. The next year, she placed second in another public speaking contest – this time at the Bessborough school commencement exercises, sponsored by the Leaside Lions Club.
Isobel was just getting started. In February 1943, the motion picture studio MGM came to Toronto as part of a North American-wide search for a young girl to star in its upcoming film National Velvet. Of the more than 500 candidates auditioned, Isobel was among the half dozen who made the short list. The London Daily Telegraph and other sources later reported that she was offered the lead role but turned it down to pursue a modelling career – opening the way for another aspiring young celebrity, named Elizabeth Taylor, to get the part.
Making it big in the Big Apple
By 1946, Isobel had left Bessborough P.S. (and Leaside) and was attending Northern Vocational School (now Northern Secondary School). Her modelling career was taking off, and her photo had already appeared in several Canadian newspapers – most notably the Toronto Star. Seeking wider horizons, she went to New York City in 1947, where she was hired by the Ford Modelling Agency. She quickly established herself as a top fashion model and cover girl, appearing in such prestigious publications as Harper’s Bazaar and Vogue, and working with photographer Richard Avedon, who became a life-long friend.
Isobel now went by the name “Liz” Benn, and it was as Liz Benn that in 1948 she was assigned to do a photo shoot in Jamaica that would change her life. There she met John Pringle, a former aide to the Duke of Windsor (England’s King Edward VIII) and member of one of Jamaica’s oldest and most established families. They married within a month and settled in New York City where John, with Liz’s encouragement, opened a men’s clothing store. Liz (now Pringle) continued her successful modelling career while John built the store into a thriving haberdashery catering to the rich and famous (his first customer was his old boss, the Duke of Windsor).
In 1953, Liz persuaded her husband to return to Jamaica and invest in a former sugar plantation which they built into a high-end, multi-million-dollar resort complex called Round Hill, near Montego Bay. Aided by Liz’s reputation and presence as a world-class model, the resort attracted throughout the 1950s a glittering range of guests and celebrities including John and Jackie Kennedy, Princess Margaret, Grace Kelly, Groucho Marx, Leonard Bernstein, Clark Gable, Truman Capote, Fred and Adele Astaire, Alfred Hitchcock, Errol Flynn, Paul Newman, and playwright Noel Coward. It grew so famous that in 1957, the resort was the cover story for the February 11 issue of Life magazine – with Liz on the cover. By the end of the decade, Jamaica was becoming a major post-war tourist destination – thanks largely to the efforts of Liz and John.
Running the resort, however, took its toll. While in Jamaica, Liz stopped modelling (she was earning $40,000 a year – about $450,000 today) so she could devote more time to raising their daughter, Shawn. But the pressures continued to mount, prompting Liz and her husband to sell Round Hill in 1961. They briefly moved to Switzerland and then back to Jamaica for a few years in the mid-1960s before finally relocating to London in 1967. They divorced in the early 1970s but remained friends until John’s death in 2006. Liz died six years later, on November 12, 2012. She was 83. Her obituary in the London Daily Telegraph exceeded 1,000 words.
Over the course of her life, she progressed from a Leaside schoolgirl to a global supermodel, numbering among her friends and acquaintances some of the most accomplished and famous people in the world. Bessborough School and Leaside can take pride in calling Liz Benn Pringle one of their own.