Canada’s best dressed: Embracing a style evolution

When she’s out and about in Montreal, Dominique Bertrand’s clothes always enter a room second. They’re wonderful – often spectacular – of course, but Bertrand’s fashion magic trick is the innate ease with which she wears them.

The former model-cum-editor-turned-author was born in Laval, Quebec, and whisked into the fashion world in her early 20s. Working with designers like Oscar de la Renta, Valentino and Hubert de Givenchy, she would go on to spend time in front of the lenses of Richard Avedon and Robert Mapplethorpe. “You had to be so strong and still,” she says of Horst P. Horst’s famously lengthy and gruelling sittings.

Now 68, she still holds on to the principles of suitability and fit that she picked up preparing for countless shoots and shows.

“When you model, they make you wear so many styles – every neckline, waist, and length – I know what’s not for me,” she says. She’s learned that if the colour and fabric work, a local seamstress can often tweak the fit. “A few adjustments and it will look like it’s been made for you,” she says.

Bertrand doesn’t think much of style edicts, especially ones related to age.

“If we listen to all the rules that they’re trying to impose on us, we’re going to go out in pyjamas,” she says. “Nothing will be allowed anymore.” Her latest signature is her natural grey hair. “I don’t think it makes women look older; I think it softens the visage,” she says.

Bertrand is currently writing a new novel (her 2024 book, La Caravane des Anges, is being adapted into a film) and admits she’s been to fewer events as a result. But her collection of custom dresses still comes in handy.

“When I’m stuck with what I’m writing and need to put myself in the creative mood, I dress like a princess,” she says. “I put on the most beautiful things I have and it pushes the button of creativity.”

– Nolan Bryant

“I find style is best experienced in person,” says freelance fashion and culture journalist Allyson Shiffman on a call from Stockholm, Sweden, where the 36-year-old, Toronto-born writer is currently based.

Shiffman’s preferred way of finding style inspiration has always been to soak up her surroundings, beginning in New York City as a freelance fashion journalist writing for titles including W, Interview and Nylon.

“I think developing my taste there was pretty formative because it’s a city that really values eclecticism and personal expression,” she says. “It was in the early days of Instagram, so it felt like I was free to develop my own sense of style without feeling a lot of outside pressure.”

It wasn’t until Shiffman moved to Sweden in her early 30s that her style took on a more polished edge, a result, she claims, of the Scandi penchant for minimalism and effortless dressing.

“I find a lot of inspiration in my friends and colleagues. If I see someone looking really cool, at a party, or even at the office, I’ll want to interpret it in my own way.”

She singles out Swedish painter and film director Marie-Louise Ekman as one of the most vibrant and sartorially inspiring women in her network.

Shiffman served as the fashion news director at Vogue Scandinavia for the last five years, a role that allowed her to spotlight the emerging designers who became the cornerstones of her personal style today. Dilara Findikoglu made her wedding dress, and she is often spotted wearing young Scandinavian brands such as Nicklas Skovgaard, Anne Sofphie Madsen, and Danish label Taus.

More recently, Shiffman has ventured out on her own, covering fashion and culture while working on a range of freelance projects. Among them was interviewing Giovanna Engelbert, another former Vogue editor and the global creative director of Swarovski, for a series looking back at the seven extraordinary couture gowns she wore on her wedding day. It was a project Shiffman describes as a kind of fashion fantasy.

– Nadia Pizzimenti

Creative directors bowing at the end of runway shows in all black has become a bit of a fashion trope, synonymous with the tyranny of so-called good taste (read: safe, restrained, maybe a bit boring). But looking at Alex Mill creative director Somsack Sikhounmuong’s wardrobe of breezy classics, you’ll find colour, fun and an aesthetic so closely matched to the label he designs for that he’s practically a walking poster boy for its sense of laid-back Americana.

“Everything I wear stems from the familiar, whether it’s something your grandparents might have worn or something you’d find in a vintage store,” says Sikhounmuong, who was also a design director at J.Crew in the 2010s.

When we meet for coffee in New York’s SoHo, the 50-year-old creative director is wearing olive green cargo pants and a perfectly rumpled periwinkle button-down, both from Alex Mill, and a baseball cap from the cult-popular Japanese workwear brand A.Presse.

“I just love old, familiar clothes over trendy ones,” he says.

Born in Thailand, raised in Oshawa, Ont., and New York City-based since relocating for fashion school in the mid-1990s, Sikhounmuong has a wardrobe full of colourful staples that feel like a patchwork of these influences: army jackets, sneakers, beaded jewellery and great jeans, all paired with the unseriousness of someone who’s been in the game for a while.

“The older you get, you just know what you feel great in and what you look great in,” he says. “I just don’t care enough to try to be something that I’m not anymore.”

Sikhounmuong attributes much of this confidence to his time at J.Crew during its heyday. “The people around me dressed similarly, and we fed off each other,” he says. “‘I thought, ‘Okay, I think I found my place.’”

When I ask who Sikhounmuong’s ultimate inspirations are, he references Belgian designer Dries Van Noten and a 2001 photo of actor Matthew McConaughey wearing a black T-shirt with a sarong and flip-flops.

“If I could walk around in a sarong all day long, I would,” he says.

– Randi Bergman

Emmanuel Uddenberg was on track to become a Bay Street banker when an outfit transition video he posted on social media went supernova.

Since then, the 26-year-old Toronto creator has made a career out of sharing his minimalist style and home decor online, attracting partnerships with brands such as Dyson, Givenchy and DeLonghi. (Being self-managed, he also gets to flex his business school chops).

“I went from having a private Instagram, private everything, to having so many eyes on me,” he says of his 220K-plus followers.

It isn’t hard to see why: Uddenberg has mastered the art of aspirational everyday dressing, with the consistency of what could be considered a uniform. He largely adheres to well-tailored basics in neutral tones such as brown, black, grey, denim and white.

“There’s still a lot of intention behind it, even though it may just be an all-black outfit,” he says. “I try to elevate it through silhouettes or interesting pieces.” That might come in the form of a big slouchy bag, pointed toe brogues or a sleek metal bracelet watch.

Does he ever feel pressured to switch up his understated, logo-free style, particularly in such an oversaturated influencer landscape? Not really.

“I do try to spice things up here and there, but I feel like it all exists in the same realm of being minimal and true to me,” he says. Occasionally, Uddenberg receives comments asking him to wear more colour, “but 90 per cent of my audience understands that’s just not me.”

He’s a fan of New York men’s-wear label Daniel Simmons and favours the easy, clean silhouettes of brands such as Our Legacy, Lemaire and Jil Sander. But Uddenberg’s earliest and most enduring style influence is his mother, Sonia Martin, with whom he shares his restrained sensibility, partiality to darker colours and love of a good bag.

“I steal her bags, she steals my bags,” he says.

– Haley Steinberg

Lydia Okello was the kind of kid who obsessed over what to wear on the first day of school and relished dressing up.

“I fantasized all August getting ready for how epic my first day outfit was going to be and trying to convince my mom to buy me platform Spice Girl shoes,” says the 36-year-old writer, model and digital creator. (Growing up, the Vancouverite’s nickname was “Imelda Marcos,” the former First Lady of the Philippines who was known for her extensive shoe collection).

Okello’s parents, immigrants from Uganda, fed this interest in fashion – particularly their father, who has since passed away.

“My dad, I think because he was raised in the British era of Uganda, was very preppy,” they say. “He loved knits, loved collared shirts, loved polos [and] always wore trousers over jeans, or slacks.”

Okello’s style is a mash-up of English prep and bold colours and textures, such as lemon-hued knits and mixed-plaid skirts from brands such as Simone Rocha and Cawley. It’s evolved as they’ve moved into their 30s and become more confident in their style sensibility.

“When I first started posting outfits, I dressed very femme and vintagey,” Okello says. “I was really obsessed with Lula Magazine and Zooey Deschanel, and I wanted to be that kind of 1950s, 1960s archetype.”

Realizing they were non-binary shifted how they think about fashion.

“It gave me way more freedom, because I didn’t feel as narrow about what I could wear.” They feel more comfortable expressing their masculine side as well as the contradictions of their style.

“I think there’s a part of my style that would be perceived as extremely feminine. I love tulle, I love ruffles, I really love the colour pink,” Okello says. “But I love those things paired with hardness and a bit of an edge.”

– Haley Steinberg

When personal stylist Irene Kim decided to split her time between Toronto and Paris, she rejected a total wardrobe overhaul.

At 45, confident in her style and unbothered by transient trends, she relied on an internal compass to help her sense of style adapt. “It’s never about moulding into some caricature of a city,” she says.

For Kim, ease doesn’t equal casual; it is a function of cut and proportion. This philosophy was tested when her beloved Tibi Calder sweatpants, the centrepiece of her Toronto wardrobe, had no place on the streets of Paris, where athleisure is virtually non-existent.

Instead of parting with them, they were relegated to travel days across the Atlantic. Replacing them with sculptural denim allowed Kim to stay grounded. It’s a choice that respects the Parisian dress code while incorporating the architectural silhouettes that help define her style DNA.

The city’s year-round transitional weather also caught her by surprise. While Canada demands dressing for extreme seasons, Paris requires trading heavy knits for breathable cotton layers. This shift meant updating her retail preferences. Her usual Toronto stops at COS have been replaced by visits to the Parisian label Soeur, where she sources foundational pieces.

Kim’s excitement for Ashlyn, the New York label helmed by 2025 CFDA/Vogue Fashion Fund winner Ashlynn Park, has made it an anchor for a closet caught between two time zones.

Ultimately for Kim, style reinvention is less important than staying true to yourself. Confidence comes from clothes that fit well, feel good and remain functional. When those principles align, your wardrobe will feel grounded wherever you land.

– Santanae Luzige

As the founder of Model Citizen, an iconic Dundas West boutique that defined local retail for over 15 years, Julian Finkel is a true pillar of the Toronto fashion scene.

Today, his focus is Panther City Coffee, the 9-to-5 persona of west end music venue the Piston. He jokes that his daytime schedule is “bonkers” for a musician used to nightlife, but it connects him directly to a shifting style landscape.

These days, that means watching the cool kids come in for afternoon matcha – including his kid Luca and their crew – sporting giant fur hats, bright pink hair, and rainbow-dyed bangs.

Observing the younger generation experiment reminds Finkel of his own style evolution. At 62, his approach to getting dressed is anchored in a Shambhala Buddhist philosophy: clothes are your armour, and dressing cleanly is an expression of respect for yourself and others.

For Finkel, that mindset is best expressed in a well-cut suit. When performing under his musical moniker, Julian Fuego, he brings that same philosophy onto the stage, injecting sharp tailoring while adding a rebellious edge with an Italian neckerchief or a pearl earring gifted by his son, John Wolf, who sourced it from Kensington Market’s Courage My Love.

When asked for style advice, Finkel refuses to hand down rigid rules, insisting kids wouldn’t listen anyway. Instead, he is inspired by their curiosity and love of vintage, championing the independent Toronto spots feeding that creative spirit. He praises Kensington vintage staples like Exile, the custom tailoring at Sydney’s, and Absolutely Fabrics, where he is excited to explore its new men’s-wear offering this fall.

For Finkel, keeping style alive is a genuine act of joie de vivre. Ultimately, aging well simply means you haven’t given up.

– Santanae Luzige