Chris Nicholls

When Hilary Weston, former lieutenant-governor of Ontario and matriarch of the second-richest family fortune in Canada, leans in to speak, her clear, plastic, stick-figures earrings dangle. “Aren’t they fun!” she laughs. “Everybody adores them—my grandchildren . . . And everybody wants to tear them off my ears.” They’re made by Miu Miu, the Prada offshoot whose appeal skews so young its 2011 spokesmodel was 14 years old. And yet on Weston, who is 71, they’re somehow fitting. Although she hides her face behind oversized shades, Weston seems none the worse for wear for having hosted an art exhibition the night before and presided over a champagne-fuelled after-party.

She’s sitting on the courtyard balcony of the Westons’ Florida home in Windsor, the country-club gated community—complete with art gallery—in Vero Beach that she and her husband, Galen, founded in 1989. According to its planner, Andrés Duany, it’s “a little odd” to have “an emphasis on culture in a holiday place. But that’s the personality of the Westons.” Continue…