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
The model strikes a pose by the pool in a beige knit sweater, a burnt-orange skirt and suede moccasin boots.
2015
Acting casual in high-waisted leather shorts and gold heels while BTS for a Sprite campaign.
2016
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
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
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.
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
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.
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.
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.
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.
She opted for a multicoloured, cut-out dress by Fausto Puglisi in Miami for a Sports Illustrated event.
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