Of all the parties that the late Posy Chisholm Feick threw in her lifetime of party throwing—parties in Rome, in Jaipur, in Cuernavaca—the one she threw here in Toronto, her hometown, in December 2006 may have been her masterpiece. She called it, grandly, Posy’s Venetian Fantasy.

Posy hosted the event at the Palais Royale, the dance hall at the foot of Roncesvalles Avenue where Duke Ellington and Count Basie performed in the 1930s. Assisted by Sinclair Russell, Toronto’s pre-eminent event planner, she chose a red and gold colour scheme. Red tablecloths topped with red glass urns were placed on each table. Sixteen mirrored balls hung above the dance floor. A big band played, and ballroom dancers, hired for the occasion, glided across the floor. Three food stations each offered samples of different cuisines, and the bar, modelled after Harry’s Bar in Venice but renamed Posy’s Bar, served bellinis.

Posy received her 400 guests seated on a bar stool, a bellini in hand. She wore a Versace jacket and bejewelled trousers, which covered the cast on the leg she had recently injured in a fall. A mere busted leg wasn’t going to spoil her fun. “Posy looked regal,” says Charles Pachter, who was one of the guests. “Like a queen, but still approachable, like your best friend.”

After dinner, the lighting changed to a deep red: Posy and Russell had conjured their own Dante’s Inferno. Guests were handed devil’s horn headbands, a DJ blasted disco tunes, and go-go girls and boys shimmied on pedestals. Peter C. Newman, who was also there, remembers that several guests had arrived in drag. “They could really dance,” he says, “instead of doing the listless Rosedale shuffle.” It wasn’t until a quarter to four that the last guests straggled away. Everybody would spend the next few days talking about that night.

People have been talking about Posy all her life. She was born in 1923 into Forest Hill gentry and always lived among the establishment, but the way she behaved wasn’t what the village expected of its upper crust. Posy refused to allow either her upper-middle-class status or her gender get in her way.

In the 1950s, most women with her lineage gave up their careers (if they’d bothered to develop one), stayed home and looked after their children. Not Posy. She had adventures on four continents. She worked as a foreign correspondent for two newspapers and became a style icon in socialite circles in Toronto, New York and Rome. She wore saris long before they were fashionable among North Americans. She married three times, each time to a man wealthier than the previous. She shaped her life in ways that were radical for the period. She was a trail-blazing pre-feminist, the kind of feminist that includes touches of both Auntie Mame and international party girl. Until she died last summer, she had spent eight decades shocking Toronto.

Posy’s given name was Rosemary. According to family legend, when her toddler brother, Scott, tried to say Rosie, it came out Posy and the name stuck. She spent her childhood at 36 Forest Hill Road, the grandest house on the street, maybe in the entire village. Her father, Robert Fennell, practiced mining law on Bay Street and chaired the Royal Ontario Museum and St. John Ambulance.

She first went to Bishop Strachan School, then to a girls’ boarding school in Cobourg called Hatfield Hall and finally to Forest Hill Collegiate. As Posy told the story, she got kicked out of all three for transgressions involving boys. Her version is probably two-thirds accurate. (In the late 1930s, nobody was asked to leave Forest Hill Collegiate for any offence short of homicide.)