10 of the Most Stylish Canadians Right Now

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We take a look at a few Canadians who are putting a sartorial stamp on Canada with their own unique sense of style. 

Scroll through our slide show below for our picks of stylish Canadians.


GQ magazine, the men’s style bible, anointed him last year with a place on their list of The 13 Most Stylish Men in the World Right Now, citing him as one of the best dressed world leaders. Not unlike his father, Pierre Trudeau, who brought a sartorial style that was a breath of fresh air to the staid air of politics when he was Prime Minister of Canada. But while not so much a fashion risk-taker as his dad – who was prone to capes and fedoras – the younger Trudeau, nonetheless has swagger when it comes to his wardrobe. He cuts a sharp confident figure, whether he’s in a three-piece suit at the White House, a tuxedo at Buckingham Palace or a traditional sherwani at the premiere of the film adaptation of Salman Rushdie’s Midnight Children at TIFF. And he can rock a Canadian tuxedo – head to toe denim – like he did at the Tragically Hip’s final concert in Kingston, Ontario.

One of the reigning supermodels of the 1990s, her off-duty style was high octane glam and she looked every bit as chic as the many fashion magazine covers she graced. Over the years as she retreated from the runway, she honed her style to a striking simplicity that whispers quiet luxury.

She was part of a cabal of women in Toronto known as the Glitter Girls in the high-flying days back in the 80s. These philanthropic women lunched and shopped but also threw the most glamorous fundraising balls the city had seen. Her wardrobe was comprised of carefully curated couture pieces – which she still wears to this day. Proof that once you discover your true style, it should last forever.

GQ magazine and multiple blogs obsesses about his style, whether he’s wearing a scalpel sharp suit or the most perfect t-shirt. But the actor is a masterclass study in effortless dressing whereby he deftly mixes the classics with contemporary. With his sharp side parted hair and trim beard, his sartorial signature is clean, spare and masculine with just a hint of retro. And occasionally he throws in a wild card – like an unusually coloured suit or a ruffled tuxedo shirt.

The coolest ambassador Toronto ever had, the rapper/singer/songwriter straddles the style divide with the hippest urban wear but pulls out the big gun suitings when he needs to look dapper for the red carpet events. Flexing his fashion muscles, he has been quietly and strategically opening OVO stores, which carries his clothing label. With outlets in LA, New York and Toronto’s hip Dundas Street West, he’ll be going up against some of the world’s biggest luxury labels in Yorkdale Shopping Centre, where he will open his next store later this year.

Finally joining her peers in the fashion merchandise game, the chanteuse is about to launch an accessories line bearing her name later this year. Perhaps this is why she has revved up her style game lately; attending two of fashion’s major summits – the couture shows in Paris and the MET Gala in New York. While her Las Vegas concerts fittingly feature her performing in an array of dazzling outfits, Dion also turns up the style wattage off stage, be it on the red carpet or the streets of Paris.


The Montreal twin brothers are co-founders of Want Les Essentiels, an uber-cool accessories line which includes a range of stylish travel bags and cool sneakers, which have garnered an international following. The duo’s personal aesthetic is one that is pared down, ultra-modern and sleek and makes them street style photo bait whenever they show up at the menswear trade shows in Florence.



The NHL hockey star has a slick sense of style off the ice which often shows him in sharp suitings and he’s a firm believer in the theory that it’s better to be overdressed than underdressed. No wonder Montreal retail chain RW&CO keeps signing him up to front their ad campaigns.


Philanthropist and wife of telecommunications scion Ed Rogers, cuts an ultra-feminine image wherever she goes with her signature swept-to-one-side hair style and sports a healthy appetite for the fashion world’s major labels. But she also supports the local talent – not just by wearing their clothes but helping to ensure there is a future for the Canadian fashion industry – with such endeavours as The Suzanne Rogers Fashion Institution at Ryerson University and her significant cash prize and award at the annual Toronto Fashion Incubator New Labels Show.

Whether or not you’re a fan of his bombastic style, you have to hand it to the man; he consistently sticks to a fashion playlist of wildly colourful and creatively patterned blazers, which single-handedly brings sartorial flair to the game of hockey. As the co-host of Coach’s Corner on CBC’s Hockey Night in Canada, he has created a signature look over the years that is completely original and instantly recognizable. A rarity in today’s world of manufactured style.