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Toronto’s Best Dressed: Elena Soboleva

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Toronto's Best Dressed: Elena Soboleva

Dressing for a theme party can be a trick: ignore the wardrobe instructions and risk looking indifferent; go too far and one may as well bring along a plastic pumpkin for trick-or-treating. This week’s best dressed—spotted at Rethink Breast Cancer’s Prohibition-themed Romp at the Burroughes Building—did a fresh take on flirty flappers. Here, the aspiring gallerist explains why the perfect outfit is like a work of art.

Where did you buy your dress? It’s rented from 69 Vintage on Queen. I didn’t even realize they rented their stuff, but it seemed like a good option for such a memorable dress.

Are you a fan of the flapper era? Sure, but I mostly enjoy dressing for a theme and being creative with it. I knew everyone was going to be wearing that classic tasselled flapper dress, so I chose something that’s a little different. I work at an art gallery—for me, putting together a great outfit is like curating a great show.

When do you think your dress was first worn? I’m not sure if this dress is from the ’20s, but it has a sort of delicate Daisy Buchanan vibe, which I love. So maybe it was worn to one of those fabulous parties.

Did you already own the feathered shoes? Actually, I grabbed the feathers this afternoon and attached them to my shoes and hairpiece. The shoes are just basic Nine West. I was listening to Chicago while I put everything together, which really helped get me in the mood.

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Courtney Shea is a freelance journalist in Toronto. She started her career as an intern at Toronto Life and continues to contribute frequently to the publication, including her 2022 National Magazine Award–winning feature, “The Death Cheaters,” her regular Q&As and her recent investigation into whether Taylor Swift hung out at a Toronto dive bar (she did not). Courtney was a producer and writer on the 2022 documentary The Talented Mr. Rosenberg, based on her 2014 Toronto Life magazine feature “The Yorkville Swindler.”

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