Twenty years later, Canadian luxury label Greta Constantine is still thriving | Canada Voices

In Greta Constantine’s Toronto studio, racks filled with silk, wool, satin and cotton garments are instant conversation starters. More than 100 looks from the Canadian fashion label’s spring, fall and resort 2026 collection are on display, primed for grand entrances or velvet ropes. Hanging together like this, they are a study in polish and progression.

The studio, southwest of the city core, is where the brand’s co-founder Kirk Pickersgill and his team turn bolts of fabric into something precise and personal – custom pieces for clients across sizes and backgrounds with somewhere to be. It’s also where each collection is born.

For those who want to buy off the rack, the items – mainly evening wear and elevated takes on daywear and workwear – can be found at luxe retailers such as Holt Renfrew.

The standout features include vibrant peplum details, saturated colour, dramatic sleeves and striking shoulder shapes. These touches are paired with modern Greek and Roman silhouettes – draping, flowy outlines that look effortlessly designed – and effortless to wear: youthful, celebratory or party-coded for a woman of any age.

The current collection marks a confident evolution, one that reflects a milestone year for the fashion house. Twenty years in, it stands among the few Canadian luxury labels not just enduring but thriving, despite challenges shaped by sourcing constraints, economic pressures and the persistent notion that Canada lacks style.

One of the greatest achievements is that every piece is designed and made in this country. Yet the brand has made its mark at home and beyond, with clients in Europe, the U.S., the Middle East and on the red carpet. Cynthia Erivo, Janelle Monáe, Halle Berry and Gal Gadot have worn the label’s chic offerings and repeat fans include Sarah McLachlan and Yara Shahidi.

Greta Constantine’s origin story begins in Toronto, where founders Kirk Pickersgill and Stephen Wong spent their 20s dreaming and dancing at a time when the city pulsed with raves, warehouse parties and after-hours events – spaces where you dressed to impress. Although Wong departed from the label in 2020 to pursue a career in costume design – landing a plum job designing on Star Trek: Strange New Worlds – the label continues to blossom.

The duo had known each other for more than a decade when they decided to start their own fashion house in 2005. They drew inspiration directly from what Pickersgill calls their home city’s gold mine: its underground nightlife. “Toronto’s dance floors really had all styles represented back then. … Even though we didn’t design clothes that reflected that directly, we were inspired by the freedom of expression we saw.”

The brand took shape while Pickersgill was working in Milan with Italian-Canadian twin brothers Dean and Dan Caten, the forces behind Dsquared2. “Watching them build something global from nothing – it showed me what was possible,” he says. “Dean and Dan were my first reference point for resilience – they taught me how to solve problems, be quick.”

Pickersgill also credits the Catens with shifting the perception of Canadian cities as chic equals to Milan, Paris or New York. “Remember, this was a time when Dolce & Gabbana was the dominant force in fashion. The moment was about pieces and separates more than dresses. Special-occasion wear skewed older and was mostly tied to weddings. There wasn’t really a youthful entry point into that category,” Pickersgill notes.

Starting up as the economy began to falter before the 2008 housing collapse and the recession that followed, the twosome pushed forward with what many told them was a bad idea – if not outright impossible. They named the label after their mothers and refined a vision Wong describes as “thinking in a Canadian way but designing for a global audience.” They viewed their shared Jamaican and Chinese backgrounds as a source for shaping their perspective on the women they wished to dress.

Their first big success came through an inexpensive yet high-quality fabric that could suit a wide range of body types. “We wanted everyone to wear Greta Constantine, so using jersey for our collection was like our aha moment,” Pickersgill says. Draped into sculptural, seasonless dresses, jersey became a defining material for the brand. So transformative was its use that the pair earned the nickname “the Jersey Boys,” even though it made only a cameo in their fall/winter 2006 debut (alongside looks in four-way stretch mesh) before taking a starring role in subsequent seasons.

Their approach to bringing jersey into evening wear, cocktail dressing and even the boardroom made such an impact that Vogue took notice – and hasn’t stopped since (Pickersgill was recently featured on Vogue.com). Milan-based fashion journalist and Vogue Japan editor-at-large Anna Dello Russo gave them the confidence to expand. She became a loyal wearer who encouraged them to pursue major distributors. Soon, Greta Constantine was sharing retail space with Versace, Armani and Dior at retailers such as Harrods, Holt Renfrew and Henri Bendel.

“It was a bunch of breakthroughs happening all at once,” says Pickersgill of those first four years – from 2006 to 2010 – a time when succeeding in the fashion market was nearly impossible without roots in Europe or New York.

When it came time to produce a runway show in Europe, Wong says they maintained an independent and inclusive mindset. “We’re people of colour, and we remember when Yves Saint Laurent sent out platoons of Black models throughout the sixties, seventies and eighties,” he says, noting figures such as Mounia Orosemane, Iman and Pat Cleveland. “We wanted to do the same with the women we worked with – all Canadian models – so we flew them from Canada to Paris for our spring 2016 collection.” Names such as Kassandra Gray and Herieth Paul still model for the house.

About the brand’s long-running success, Pickersgill says the greatest inspirations come from their clients, both on and off the red carpet. “We just kept listening to customers and asking them what they wanted,” he says of the silk, sheer, satin, felt and melton pieces shaped by function, form and fantasy. Arguably, Greta Constantine has mastered the art of getting dressed up without sacrificing ease.

Krystal Koo, a Toronto-based real estate leader, socialite and philanthropist, has been wearing the label since 2009. Her first purchase – a one-shoulder dress designed in silver silk gazar called the Jaime – had an immediate, empowering effect. “I’d never spent that kind of money on an outfit before, but when I started wearing Greta Constantine and working with Kirk, it was worth more than I paid. It was such a turning point for me – I was finding myself and my own style, and these clothes helped me do both,” she says.

Since then, Koo has worn the brand for defining personal and public moments: a custom kelly green silk cape for the first edition of the UnMet Gala, the charity she founded to support underserved Toronto communities. Pickersgill also made a bespoke look to celebrate her pregnancy at the Canadian Arts & Fashion Awards – a deep purple two-strap silk wool gown he named the Koo Dress. She has also hosted numerous gatherings for the label at her Toronto home, becoming a fervent supporter long before a wave of celebrities followed.

When Meghan Markle wore the brand’s green Kace skirt in Belfast in 2018, ahead of her wedding to Prince Harry, the spotlight fuelled intense sales. “After that photo hit Vogue and other outlets, we sold more separates that week than we normally do in a year – we’re still selling it,” Pickersgill says.

The label’s star-filled roster also includes Angelina Jolie, Victoria Beckham, Viola Davis and Angela Bassett, who wore a striking white jumpsuit at the 2023 NAACP Image Awards and a pink-and-black ruffled gown at the 2021 Emmys. (“Stephen and I had a baguette and tea with her in Paris,” Pickersgill says.)

At the Junos last month, McLachlan wore two dresses – a confection from Greta Constantine’s 2026 resort collection for her arrival and an archival dress plucked from fall 2024 for her performance. In an e-mail explaining her choices, McLachlan wrote: “Greta Constantine consistently puts out bold and fabulous well-tailored pieces that fit me beautifully. The dresses I wore for the both the performance and red carpet hugged in all the right places yet were so comfortable and flowy, too. I was drawn to the artistry.”

One of the most defining moments in the brand’s history hangs framed in Pickersgill’s office: U.S. poet laureate and activist Amanda Gorman wearing a yellow puff-sleeved Keele gown (named after a major street in Toronto) on the cover of a February issue of Time magazine’s March 21, 2021, issue. Gorman explores gender equity, systemic racism and climate change in her work.

It was a rare occasion when Time magazine credited a designer for its cover, says Pickersgill. “It was important that every element represented Black excellence. … It was the first time I cried in the history of Greta Constantine,” Pickersgill recalls. “I still point to that photo with my team and say, this is something we can talk about for generations.”

The Gorman moment arrived just as the brand was navigating the challenges of the pandemic. With events on pause and Wong’s departure, Pickersgill temporarily reduced his team from 12 to two – eventually rehiring 12 – while pivoting to relaxed fit dresses, mask-making and intimate wedding pieces to stay afloat.

Jesse Greene, who began as an intern 16 years ago and is now the brand’s general manager, says those challenges were eclipsed by renewed demand. The label went on to dress Julia Roberts at Cannes, Abbott Elementary’s Sheryl Lee Ralph and Quinta Brunson at the Emmys, and Samira Wiley during the rise of The Handmaid’s Tale. About Greta Constantine’s aesthetic, Ralph writes in an e-mail, “There is a strength in the structure, a boldness in the silhouette and a grace that allows me to feel both powerful and complete.”

Yet the brand’s bestselling piece remains the Loanne dress, an off-the-shoulder design named after a seamstress who Pickersgill worked with during his early career at well-known Canadian brand Comrags. “So many of our hits are named after women we know – not celebrities, but women who are stars to us in Canada.” This includes model Jacqueline Summers, who inspired the Jac jumpsuit, and the Susie dress, a tribute to Canadian fashion editor Susie Sheffman.

About the label’s continuing success, Toronto-based stylist Zeina Esmail, who has worked with the brand for eight years, credits Pickersgill’s fierce and independent vision. “Kirk never conceded to external pressures and stayed focused on his signature aesthetic,” she says, noting he’s already working on approachable and covetable looks for 2027.

“He continues to marry exaggerated silhouettes with femininity – which is why women globally love Greta Constantine and want more of it.”