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Toronto’s Best Dressed: Jessi Cruickshank

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Toronto's Best Dressed: Jessi Cruickshank

Given its status as the unofficial “it” party of the season, the Innovators Ball is worth a second Best Dressed selection. Here, MTV’s reality TV starlet Jessi Cruickshank wears a budget-friendly gown—part of the new Matthew Williamson for H&M collection—and explains the possible pitfalls of prints.

That dress is a coveted item. I’m guessing you weren’t one of the people lining up at 4 a.m. outside the Eaton Centre to get first dibs. No, although not to say that I wouldn’t. I was lucky enough to get a preview of the collection and pick a few items. I thought all these ruffles would be great for a ball.

Who else should do a collection for H&M? I would love to see Giambattista Valli do one. His over-the-topness for regular people would be awesome.

Prints are big this season. Is there one that you try to avoid? Cheesy prints are rampant these days—Sarah Jessica Parker brought them back. A good floral is hard to find. It’s got to be big and bright, and still you can end up looking like a granny. Or a couch.

What trend is past its expiry date? Leggings are a tough one to pull off. There should be a rule about covering the bum and the frontal area.

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Your claim to fame is weighing in on the inane antics on The Hills. Is there such a thing as too tanned? Too blonde? Too many nose jobs? Yes, yes, yes. You can’t buy sex appeal. You can have boobs sewn on your chest, buy your hair, buy your nose, but it’s not going to make you sexy, Heidi.

What Torontonian would you like to see with his or her own reality show? Jay Malinowski from Bedouin Soundclash. He’s a good-looking guy and girls are always throwing themselves at him. It can be awkward to witness but also fun to watch.

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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