Street Style: The Canadian Arts and Fashion Awards (featuring one of T.O.‘s Real Housewives)

We asked some of the best—and most bizarrely—dressed at this year’s CAFA gala to explain their outrageous outfits. Here, 10 of the boldest looks we saw.

Odessa Parker

Fashion editor, Globe and Mail “My dress is custom Philip Sparks. I picked the fabric, which came from France. There’s actually a matching cape, so if you come find me later, I’ll be wearing that. It’s a bit of a wizard vibe. My shoes are John Fluevog, and this a vintage Jeanne Lotti purse—so I’m committed to Canadian, even with vintage.”    

Dwayne Kennedy

Fashion director, The Collections “I obviously wanted to wear Canadian. One of my favourite designers is Rad Hourani, who gifted me this piece. I would describe the look as unisex—that’s Hourani’s whole mandate for his brand. It’s a vest and I’m wearing it in the traditional male version, which is to belt it in the back, but you can tie it in the front to make it more feminine. It’s very versatile.”    

Roxy Earle

Real Housewife “I wanted to wear the first ever CAFA winner, which was DSquared. This is my first CAFA Awards, so it felt right. Do you see how there are Canadian flags on my shoes?"    

Simona Schnaider

Socialite “My dress is Erdem. He’s my guest at the table, so of course I chose one of his dresses.”    

Vincent Law

Contributing writer, Vogue Italia “This is by Laurence and Chico, Canadian designers based out of Vancouver and home-based in Paris. It’s all about supporting emerging talent. They’re very quirky—they love avant-garde pieces. I try to dress for my personality and this feels playful and unique.”    

Caillie and Sam Beckerman

Fashion bloggers “We’re wearing Michael Kale—it’s very rock-and-roll Grecian. He custom made them for us. I’m not sure how we decided who was purple and who was brown.”    

Ainsley Kerr and Sabrina Maddeaux

Jewellery and art consultant, journalist Kerr: “My dress is Mikael D. I actually bought it to wear to last year’s CAFAs, but I changed my mind at the last minute. I feel like I’m channeling my inner Disney princess—very Cinderella.”

Maddeaux: “My dress is Stephan Caras, right off the Fashion Week 2017 runway. I’ve been a fan for years, and always love an opportunity to show that Canadian design can be about more than just parkas. It can be elegant, avant garde and on par with the major European labels.”    

Deseiye, Kelly Claman and Jonathan Hooper

New Canadian designer, owner of Kelly Claman branding agency, photographer Deseiye: “I wanted to look like Big Bird meets Game of Thrones. I’m a makeup artist, so I did the makeup myself.”

Claman: “It’s vintage Nightcap. I feel like this is classic, timeless.”

Hooper: “All Canadian: Denis Gagnon on top and Cut and Sew on the bottom. The vibe is casually-uncasual.”    

Leigh Lezark

DJ “It’s Greta Constantine. We’re deejaying tonight, so I wanted something fun.”    

Sergio El-Azzi

Fashion blogger “This is Hendrix Roe, which is Canadian. I figured tonight was a night to step out of my comfort zone with bright blue. My inspiration is Maharaji prince.”