The lights are low, and the room is rammed. The crowd at Soho House Toronto, the local outpost of the global network of private clubs, is a curated coterie of stylists, influencers, and nightlife personalities. The August evening air is cool enough to vape outside without breaking a sweat. Inside, the fashion designer Joey Gollish is holding court, his pearl-white Saint Laurent penny loafers gently glowing by the dimly lit bar. But we’re not here to celebrate Mr. Saturday, Gollish’s edgy, nightlife-inspired clothing brand. We’re here for the fiftieth anniversary of Roots, the outdoorsy Canadian label, and Gollish is its first ever creative director-in-residence.

Since founding Mr. Saturday in 2017, Gollish has become a rising star in Canadian fashion. He has crystallized his vision of the globe-trotting, grown-up partier with his mix of sharp tailoring and sleek, graphic streetwear. His label counts high-wattage artists like Nicky Jam and Asake as fans, and fashion insiders and celebrities fill the front row at his Paris Fashion Week shows. The brand is also stocked by Ssense, the cutting-edge e-commerce giant known for styling emerging labels alongside luxury behemoth brands like Prada and Loewe.

In October of 2022, Gollish was crowned the Menswear Designer of the Year at the Canadian Arts and Fashion Awards. Two months after winning the award, Mr. Saturday dropped Roots Saturday Airlines, a streetwear-inflected capsule collection with Roots that was “inspired by jet set culture” and referenced Roots Air, the brand’s short-lived airline. (Mr. Saturday and Roots have had a symbiotic relationship—Gollish has long manufactured his leather pieces for Mr. Saturday using Roots leather. Some pieces, like a baby-blue suede overshirt, even feature the Roots label inside.) The collaboration aimed to reposition Roots as a culturally relevant brand for fashion-obsessed zillennials—those on the cusp of millennials and Gen Z—who are fluent in both streetwear and luxury.

Roots won’t disclose sales numbers, but at the opening of the Toronto location of the upscale retailer Kith, I spotted a young man wearing an oversized T-shirt from the collaboration. The collaboration’s success resulted in Meghan Roach, the CEO of Roots, establishing a creative director position for Gollish in March 2023.

Roots and Mr. Saturday are two brands that appear to have diverging identities. Roots represents wholesome Canadiana craftsmanship and leans into our woodsy national persona; Gollish sells an image of louche, after-hours hedonism and is friendly with the Weeknd. If you wear Roots to the cottage, you wear Mr. Saturday to the club. The challenge for Roots is to infuse a family-friendly legacy brand built on salt-and-pepper sweatpants with an Ssense sensibility. Can Gollish make a mass market Canadian heritage brand cool?

Childhood friends Michael Budman and Don Green co-founded Roots in 1973 as a premium outdoor apparel brand after meeting at summer camp in Ontario’s Algonquin Park a decade earlier. In 1985, the brand launched Roots Beaver Athletics, a line that debuted the now-iconic beaver logo, which suburban middle-class families quickly adopted as their uniform. In 2015, Roots sold a majority stake to Searchlight Capital, a private equity firm, to grow its international presence. Two years later, Roots filed an initial public offering.

Today, the over $34 billion Canadian apparel market has fallen flat thanks to economic headwinds like inflation and the housing crisis which have impacted consumer spending and supply chain issues. Roots is no exception and has financially plateaued. But the brand still maintains a strong retail presence in Canada, operating 100 stores across the country, along with two in the United States and more than 100 partner-operated stores and third-party retail sites across Asia. Retail analyst Bruce Winder praises the brand’s “inspiring” stores, excellent product quality, and design but says it lacks the buzz necessary to compete in today’s environment. “I feel like they’re kind of too quiet, like no one’s hearing them.”

The past decade has ushered in cataclysmic shifts that have upended the fashion industry and changed the way we shop. E-commerce made designer fashion globally accessible, while fast fashion grew into a billion-dollar business, much of which is built on designer dupes at a fraction of the price. Social media disrupted traditional advertising’s influence and reach. Fashion influencers speak directly to consumers and suck up the robust advertising budgets that once funded the pages of Vogue or GQ. This paradigm shift leaves mass market brands like Roots in a tricky spot. If they go too fashion, they risk alienating loyal customers. If they play it too safe, they risk irrelevance.

There’s a deeper sociological undercurrent reshaping retail: growing income inequality and the hollowing out of the middle class. “You’re either watching every dollar or you’re pretty affluent,” says Winder of today’s two main consumer groups. The clothing retail industry is increasingly polarized between fast fashion brands like H&M and luxury brands like Prada and Gucci.

Some brands have survived by evolving. Canada Goose, for example, has gone way upmarket—most of its parkas are now priced around $1,500—with celebrity endorsements and wide distribution to match. But Roots’ heritage of wholesome Canadiana is both an asset and a liability. Roots appeals to its customers by walking a fine line between affordability and quality, between comfort and style. The beaver is core to Roots’ DNA, but it’s started to limit the brand’s ability to reinvent itself for the modern world.

At the Roots factory last year, Gollish excitedly flicked through racks of vintage varsity jackets and archival leather pieces. He was looking for design inspiration for future products, but he was also trying to determine which pieces might be worth reissuing. He pulled out a Sport Root shoe, a retro sneaker with a subtly orthopaedic shape. Gollish was handling samples of the shoe in a few earthy shades, debating which to release first. (Putting my shopper hat on, I pushed for slate grey-green, but polite silent nods from Gollish and Roach told me that shoe would likely not be produced.) The shoe was eventually rereleased in the brand’s unique cedar-brown leather. It’s a shrewd choice; the shoe has mass appeal in our nostalgia-driven moment but is recognizably Roots. You could just as easily imagine a twenty-five-year-old wearing the Sport Root with wide-leg Carhartt jeans as you could their father. Several of the online comments on the product website praise “the return of this iconic footwear” that’s “just as good as 1976!”

Gollish is an idea generator, commercially savvy and familiar with the brand’s history and position in the market. But it’s not yet clear how these ideas and knowledge will translate to a larger execution.

In his Roots Saturday Airlines collection, Gollish injected Mr. Saturday’s streetwise attitude into Roots’ recognizable athletic wear, successfully merging these two identities to create something fresh for a specific audience. But browsing the Roots website, social media, or stores today, there appears to be little difference between old Roots and new—yet.

Gollish likens being a creative director to DJing: sampling and remixing existing ideas, presenting them in a novel way that still appeals to a mass audience. “It’s not always [about] making something new,” he says. It’s about showing people the best product “at the right place and the right time.” That’s why the design of the physical stores and the website haven’t changed much. “It’s an iterative process,” Gollish concedes.

Roots regularly releases new products, but they’re not aiming for a total reimagination of the brand’s core offerings. Gollish’s role is to tinker slightly with Roots’ DNA, to market their existing products for today’s audiences, and to lodge Roots more firmly in contemporary culture.

Roots’ strategy seems to be to take an ordinary item and, as Tyra Banks would say, make it fashion. To realize this, Gollish installed his cadre of creatives, including a new in-studio photography team and Bobby Bowen, the in-demand Toronto stylist and editor-in-chief of Bully magazine. Bowen is responsible for contextualizing the clothes in a modern way, like pairing a hoodie with a blazer or tying a sweatshirt around the model’s shoulders for a preppy look. The goal is not to radically overhaul the product but to speak to a fashion-forward customer. New campaign imagery, diverse casting, contemporary styling, and brand partnerships also project a more inclusive brand—the message is that Roots dresses everyone, not just suburban kids. A recent Lunar New Year collaboration with Clot, a Chinese streetwear brand, sees Asian models young and old decked out in limited-edition varsity jackets and fire-engine-red sweatpants tucked into boots.

But like all apparel brands, Roots recognizes it must be culturally relevant to be commercially successful. Alecsandra Hancas, the executive director of client development and apparel, beauty, and footwear industry analyst at Circana, notes that Roots launched a size-inclusive, sustainable, gender-free collection in 2021 and released a(n obligatory) Barbie collaboration in 2023 which both Roach and Hancas agree invigorated consumer interest. Tapping Gollish is the next step in that evolution. “I think it’s going to bring that global appeal to the brand,” says Hancas. “And I think, genuinely, it feels like a very organic collaboration.”

Roots didn’t hire Gollish for a radical overhaul, but the brand needs one. And while Gollish is certainly capable of steering this ship in a new direction, beyond glimpses here and there, the final destination is just out of sight.

The glimpses we’ve seen are promising. Visual content with simple styling gestures like tying a sweater over a model’s shoulders or layering a polo under a crewneck can lend a staid brand cachet; it signals that a brand is dialled in to trends. But without a cohesive, Gollish-helmed collection, it’s hard to say whether Roots will deliver on that promise.

For now, it seems Gollish’s role draws less on his skill as a fashion designer than on his acumen as a brand marketer. At the Soho House soiree, most partygoers left with one of Roots’ leather wallets embossed with their initials. But these sensible souvenirs don’t square with Gollish’s youthful, progressive style.

Dressing the masses is a far greater challenge than designing fashion. Roots need not become Mr. Saturday, but the brand should leverage his talent as a designer as much as his marketing wizardry and rising profile as a jet-setting tastemaker. Mass brands can offer curated collections that translate runway fashion to the mass market alongside their standard stuff. Roots can—and should—do the same, and Gollish is doubtless up to the task. But they need to officiate a formal marriage between Mr. Saturday and Roots to do so.

This is where the worlds of luxury fashion and mass apparel diverge. Creative directors at storied maisons must define a brand in their own image, which often involves wiping the slate clean. In 2015, Alessandro Michele introduced his maximalist magpie aesthetic to Gucci in a complete break with the previous creative director’s proposition of understated glamour. In 2018, Hedi Slimane sent his cult of young, snake-hipped rockers down the runway for his debut at Celine, the antithesis to former creative director Phoebe Philo’s cerebral, idiosyncratic minimalism.

Mall brands have had mixed results with that approach. Gap’s cursed partnership with Kanye West’s brand Yeezy and the Parisian fashion house Balenciaga comes to mind. Even before West’s antisemitic and racist remarks tanked the project, the collaboration was marred by confusing products that represented too stark a departure from Gap’s core brand offering of products such as jeans and chinos. (In another attempt at reinvention, Gap recently tapped designer Zac Posen as executive vice president and creative director of Gap Inc.’s portfolio of brands which includes Old Navy and Banana Republic.) But Brendon Babenzien, the founder of the hip skate brand Noah, has breathed new life into the once-bankrupt mall brand J.Crew on the men’s side (his giant chinos and oversized oxfords are hits among stylish guys, but the “new J.Crew” is only sold online and in select stores). Perhaps the most successful examples are Uniqlo, whose core collections of essentials and basics are stylish and accessible, and ongoing collaborations with buzzy designers like Christophe Lemaire and JW Anderson to reach a fashion-oriented customer without breaking their bank accounts. Roots is seemingly emulating this formula: subtly dialling up the cool quotient on its core offering and recontextualizing its heritage and legacy for a digital era.

Gollish’s contract is up for renewal next March. In that time, customers should be able to enter a Roots store or browse the website and think: Did the Mr. Saturday guy design that? That’ll work with the Sport Root.

There’s a tension between clothes that pop online and those that don’t, between fashion and anti-fashion, between buying the viral handbag and wearing your dad’s old sweatshirt. These competing desires result in a mishmash of designer and vintage, of high and mass. It’s easy to imagine fashionable young people across the country—or world—pairing their parents’ vintage Roots varsity jackets with, say, white Saint Laurent penny loafers.

Roots’ heritage—as a celebration of the Canadian outdoors and craftsmanship—is a foundation to build upon, in the vein of Gap’s ’90s oxford shirts or J.Crew’s cashmere sweaters. Roots wants to be nostalgic yet modern by evolving to meet the moment without abandoning its, well, roots. The truth is: Roots may not be fashion. But that’s the key to its future.

Correction, May 14, 2024: An earlier version of this article stated that the Canadian apparel market is worth over $34 million. In fact, it’s worth $34 billion. The Walrus regrets the error.

Josh Greenblatt
Josh Greenblatt is a freelance writer and editor in Toronto. His features and essays have been published in GQ, the Globe and Mail, Maisonneuve, and more.