Hilary M. Weston, who with her late husband W. Galen Weston, played a significant role in the conception and development of the island’s exclusive Windsor community, died at her residence in London on Aug. 2 at the age of 83. She was predeceased by her husband of 55 years in 2021.  

Distinguished by her elegance and poise, Weston earned significant recognition in Ireland, England and Canada for her philanthropy and business leadership, even before bringing her exceptional design expertise to Vero Beach.

Born Hilary Frayne in Ireland, she was an elite fashion model in 1963 when she caught the eye of Galen Weston, who quickly recognized that her talents extended well beyond modeling. The couple married in 1966 and subsequently established a successful and enduring partnership in business and in their personal lives.

Hilary provided steadfast support to Galen throughout the expansion of his global grocery and retail enterprises, which ultimately extended across both sides of the Atlantic. In 1972, they relocated to Toronto following Galen’s appointment as chairman of Loblaw Companies.

She was also at his side in the late 1980s, when they collaborated to transform a nearly 500-acre riverfront citrus grove on the 32963 barrier island into what is now the distinguished Windsor community.

“Mrs. Weston was the heart and soul of Windsor. Her vision shaped every detail of this community; from its architecture and design to the values we uphold. Working with her was a privilege. Her spirit will forever be part of Windsor,” said Betsy Hanley, president of Windsor Real Estate, Inc.

Renowned for its emphasis on privacy as well as its association with polo, a sport enjoyed by Galen, his son, and grandson, even the present King Charles participated in matches on Windsor’s prestigious grounds on two occasions.

Beginning in 2012, Hilary graciously chaired and presided over the highly anticipated biennial Windsor Charity Polo Cup. Proceeds from the hugely profitable event have supported numerous Vero Beach nonprofits, funneled through the Windsor Charitable Foundation. 

Established in 2015, the foundation provides philanthropic support to charities focused on food security, housing, disability, healthcare, education, medical research, environmental initiatives, and animal welfare, and to Windsor employees facing personal hardships.

A champion of the arts, Weston and her daughter Alannah Weston Cochrane launched the Gallery at Windsor in 2002. Hilary served as creative director for the gallery, which has introduced a wealth of international contemporary artists to Vero Beach. Proceeds from visitors to the gallery have supported local arts nonprofits, including the Vero Beach Museum of Art, Ballet Vero Beach and, most recently, the Laura (Riding) Jackson Foundation.

“It was an honor to know Mrs. Weston and to work closely with her over the past 15 years. She brought a rare depth of style and creativity to everything she touched. I am truly grateful for her mentorship. Her presence at Windsor, and her friendship to us all, will be greatly missed,” said Jane Smalley, Windsor marketing director. 

In 1997 Hilary Weston was appointed as Ontario’s 26th Lieutenant Governor, becoming only the second woman to hold that position.  Throughout her tenure, she advocated for women, young people, early childhood education, volunteers, and social issues. She established the Lieutenant Governor’s Community Volunteer Award, expanded the Community Volunteer Award program, and founded the Hilary M. Weston Foundation for Youth.

Her philanthropy and services to her adopted country would earn her the Order of Canada and the Order of Ontario. Those same passions led to the creation of the Hilary and Galen Weston Foundation, which has committed nearly $150 million to charities in Canada, Ireland and the U.K.

A successful businesswoman, Hilary Weston held numerous board positions, including as the deputy chair of Holt Renfrew, a prominent Canadian luxury department store chain, and as a director of Brown Thomas & Co. in Ireland. In her role as director of Selfridges Group in the United Kingdom, she leveraged her design acumen and fashion expertise to significantly influence the strategic direction of the upscale retail organization.

An author herself, she founded the Hilary Weston Writers’ Trust Prize for Nonfiction, recognizing Canadian literary nonfiction, and the Weston International Award, for nonfiction writing globally.