From airport outfits to red carpet gowns, Winnie knows how to make a statement on and off the runway. Here’s a timeline of the Canadian supermodel’s style evolution.
2013
Winnie wears a Noir Masae Couture dress with a bold tropical print and cut-outs for her birthday celebration.
2014
View this post on InstagramNever caught off guard . #chantellewinnie #barcelona
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The model strikes a pose by the pool in a beige knit sweater, a burnt-orange skirt and suede moccasin boots.
2015
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Acting casual in high-waisted leather shorts and gold heels while BTS for a Sprite campaign.
2016
View this post on InstagramThank you @mtvema for having me as a presenter! So much fun ☺️??
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The model stole the show in a red and blue sequinned Elie Saab dress with a high leg slit and strappy heels while presenting at the 2016 MTV EMAs.
Winnie charmed her way through the British Fashion Awards red carpet in 2016, wearing a black silk gown by Baja East and metallic Christian Louboutin pumps.
2017
View this post on InstagramCasually leaving fitting.. sees paps, looks down ?????
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She was spotted stepping out of fittings in a white long-sleeve top, a leather jacket with shoulder cut-outs, light-wash jeans and black lace-up boots.
Winnie looked effortlessly glam as she stepped out with Bella Hadid. She wore a Marc Jacobs lilac satin skirt paired with a matching jacket, black turtleneck and boots.
Winnie opted for grunge chic in a shimmering black Marc Jacobs mini-dress with champagne-coloured satin details and sparkly platforms for a LGBTQ Community Center of New York fundraiser.
Later that year, she went for a more neutral-toned outfit for a ME to WE red carpet with tan trousers, a matching jacket and a white lace bodysuit.
Winnie stunned in a red Zuhair Murad gown and matching red lipstick at the Cannes Film Festival in 2017. She accessorized the look with a bold Chopard diamond chain and emerald teardrop pendant.
She attended the 2017 amfAR Gala at Cannes in a sheer and sparkly Ashi Studio dress, paired with minimal (but equally sparkly) accessories.
2018
View this post on InstagramDust yourself off and try again ?
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Winnie showed up to support her hometown team, the Toronto Raptors. Her very pink game day attire included a bubblegum Tommy Hilfiger puffer jacket, hot pink boots and a Heron Preston x Off-White shoulder bag.
The model looked angelic for her first Met Gala appearance in 2018. She wore a custom Tommy Hilfiger gown and an all-white orchid headdress made by Brittny Wood.
Winnie made an appearance in a netted Dior gown at the fashion house’s dinner with Madame Figaro during the 2018 Cannes Film Festival.
Winnie shone in another red carpet-worthy gown at the 2018 Cannes Film Festival. She wore a jewel toned Ralph and Russo off-the-shoulder gown, complete with a high slit to show off gold heels.
The model stepped out in a in a Roberto Cavalli long-sleeve feathered bodysuit and thigh-high leather boots on her way to celebrate Jennifer Lopez’s MTV VMAs Video Vanguard Award win.
View this post on InstagramHer crazy match my crazy ❤️ So happy to be home ???
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The model gave us logo-mania inspo with her Fendi boots and shoulder bag while at a Toronto Raptors game with model and BFF Shannon Hamilton.
2019
View this post on InstagramYou know what New York.. you’re too cold for me right now✌???
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Winnie gleamed as she stepped out of the car in a silver satin Galvan London dress and Christian Louboutin studded thigh-high boots for a screening party to debut the new Louboutin luxury runners.
View this post on InstagramBuongiorno Milan Fashion week! Thank you @flyprvt @puma for getting me here in style #cali
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The supermodel landed at Milan Fashion Week in a black crop top, black and white-striped track pants and a bright green puffer jacket paired with Puma runners and a Louis Vuitton duffle bag.
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The model wore an elegant royal blue, long-sleeved mini dress and matching leather thigh-high boots for an appearance on the Tonight Show with Jimmy Fallon.
Embellished gown + feathers + elaborate headpiece = Winnie channelling camp in custom Tommy Hilfiger for the 2019 Met Gala.
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Winnie looked pretty in pink at the Roman Colosseum for the Fendi Haute Couture show. She wore a pastel, gown and cape with sequin flower applique.
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She opted for a multicoloured, cut-out dress by Fausto Puglisi in Miami for a Sports Illustrated event.
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