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How many ways can a designer rework a classic pair of jeans? We count at least 20 on supermodel Liisa Winkler alone

An easygoing wardrobe of denim seems perfectly suited to supermodel Liisa Winkler. Her 20-plus-year career has focused on finding balance between her love of the simple life and fashion’s over-the-top glamour

For the better part of the pandemic, Winkler has been busy building a greenhouse in her backyard. A registered herbalist, she plans on transforming her piece of Toronto’s east end into a verdant hideaway where she can treat clients with her own remedies and teach students of all ages about the healing power of plants. “It’s been such a happy focus for me,” she says.

The 40-year-old supermodel isn’t the only runway regular who has pivoted to wellness. Miranda Kerr co-founded an organic skin-care line, Adriana Lima became a fitness expert and Gisele Bundchen has long been extolling the virtues of environmentalism and transcendental meditation. Modelling can be an intense profession that leaves its busiest stars craving balance. And once they find it, they’re often happy to pay that awareness forward. “People are asking more questions about their health and they are wanting to take it into their own hands,” Winkler says.

Winkler was an early adopter to self-care and sustainability. Back when coffee, cigarettes and all-night benders were the purported keys to supermodel success, she was practising vegetarianism and advocating for the organization, World Animal Protection. She even collected trash backstage at shows. “At one point, I actually started filling bags with all the plastic bottles that people used on set and taking them back to Canada where they could be recycled because the U.S. did not at that time,” she says.

It is perhaps a surprising sensibility for a model who rose to fame in 1999 after becoming an It girl for Tom Ford-era Gucci, a designer and a label known for an aesthetic of excess. Winkler modelled exclusively for the brand for three seasons. “I felt very fortunate to be part of that time,” she says. “Somehow I got in with Tom Ford and all of a sudden I was part of this family – the same hair people, the same stylist – Tom was always there.” Winkler was drawn to the imperfect glamour of that particular moment in fashion. “There wasn’t much makeup, and it was all about being natural – looking like you, but an amplified version,” she says. “I remember when we were shooting the campaigns, [Gucci stylist] Carine Roitfeld would say, ‘This is great, but something has to be off.’ Just a little something to set it apart.” Winkler went on to model for the likes of Balenciaga, Calvin Klein, Valentino and the Row, for whom she still appears in campaigns and fashion shows.

In her modelling work today, Winkler draws the line at wearing fur and using plastic on set but she has chosen to stick with the industry and use her platform for good. “I am just one voice, but you make personal choices and hope that the rest of the business goes that way too,” she says. “Ultimately, it’s heading to a better place because people care. The consumer cares.”

On the loose

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Get comfortable in Chloe’s retro trousers.

Chloe blouse, jeans, available through Labucq shoes, available through

Piece by piece

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Contrast stitching adds to the patchwork effect of the Dior spring line.

Jacket, trousers, available at Dior.

Lighten up

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A pale dress by Y/Project will become a summer staple, and so might the styling trick of wrapping yourself in a crisp shirt like a cardigan.

Y/Project dress, available at Ssense. Baserange shirt, available at Gravity Pope. Michelle Ross earrings, available at Michelle Ross Studio. Labucq shoes, available through

Let’s ride

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Moto-style leather accents give this Alexander McQueen duo an unexpected edginess.

Alexander McQueen jacket, jeans, available through

Full spectrum

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Layer shades of denim and chambray to create a colour blocked effect.

Ami shirt, available through Levi’s jeans, available through Stella McCartney espadrilles, available at Ssense.

Go deep

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Andrew Szewczyk’s jacket and Khaite’s jeans share a rich indigo hue.

Andrew Szewczyk jacket, available through Shirt, available at Cos. Khaite jeans, Prada sandals, available at Nordstrom.

Feet first

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A pair of Isabel Marant boots guarantee that you can sport denim from top to toe.

Isabel Marant jacket, boots, available through T-shirt, available at Cos. Y/Project jeans, available at Ssense. Michelle Ross earrings, available at Michelle Ross Studio.

Remade and remixed

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Classic blue jeans and a pinstripe suit are deconstructed and pieced together into a contemporary combo.

Kathryn Bowen jacket, skirt, available through MM6 waist belt, available through

Garden path

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Printed denim goes posh via Chanel’s floral maxi skirt.

Shirt, available at Cos. Skirt, earrings, available at Chanel.

Under cover

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Two trousers combine in one unique style. Reveal the more casual under layer or cinch the belt to hide it away.

Dion Lee top, Y/Project trousers, available at WDLT117. Laura Lombardi earrings, available at 100% Silk Shop.

Do slouch

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The season’s easier proportions are expressed in the oversized silhouette – and exaggerated turned-up cuffs – of a Gucci look.

Shirt, jeans, available at Gucci. Laura Lombardi belt (worn as necklace), available at 100% Silk Shop. Churches shoes, available at Gravity Pope.

Styling by Nadia Pizzimenti. Makeup & Hair by Jodi Urichuk for Plutino Group/L’Oréal Paris/Shu Uemura. Model: Liisa Winkler at Just Management. Styling assistant: Alex Petropoulakis.