Photograph by Ryan Emberley

This is What it’s Like to Have Brunch With Anna Wintour

It's a fashionable affair, to say the least

By Bernadette Morra

Date September 7, 2019

For 150 lucky fashion lovers, day two of the Toronto International Film Festival started with a style challenge like no other: how to dress for brunch with Dame Anna Wintour. Prada? Chanel? Gucci? Local designers Greta Constantine or Narces? Turns out there was all of the above.

The Vogue editor-in-chief and artistic director of Condé Nast had swooped into town for a precious few hours to receive TIFF’s first annual Icon Award at the Four Seasons Hotel. In and out by private jet faster than you can say Manolo Blahnik (she had to rush back for New York Fashion Week), Wintour was picture perfect in a midi-length tweed Chanel dress and her trademark semi-precious strands and blackout shades.

Wintour worked the carefully selected crowd with the silky smoothness of a politician, smiling and shaking hands, posing with Dakota Johnson who dropped in to say a quick hello, receiving accolades from co-chairs Suzanne Rogers and Sylvia Mantella with grace, and then delivering a thoughtful speech. She talked about the importance of her political and charitable work, gave a shout out to Canadian designers Tanya Taylor and Aurora James, and made it clear that she would be sitting in Serena Williams’ box at the US Open, and that Bianca Andreescu has many wonderful years ahead.

“I want to thank you not just for this award but my first and – unless I enroll urgently in a screenwriting course – probably my last film festival honour,” she said. “But also to congratulate you on the imagination that lies behind the films Toronto is supporting. I was lucky enough to see Cynthia Erivo’s breathtaking performance in Harriet. And I am so looking forward to Rosamund Pike’s portrait of Marie Curie in Radioactive, and Ellen Page’s documentary There’s Something in the Water.”

And then – whoosh! – she was gone. Leaving a roomful of women, and a couple of gents, marvelling at how the woman once dubbed Nuclear Wintour, had warmed their souls.