This Brand of the Year story was originally published in the Fall issue of Strategy Magazine. Check out the winners as they appeared online over the course of this week here.

Be fashionable, but also functional. Be iconic, but not dated. Be youthful, but don’t alienate those who’ve lived life. Be eco-friendly, but also affordable. The goal to be “everything to everyone” is a tightrope that many companies walk. Tilley being one of them. This is the story of how the heritage brand found its feet.

It all began in 1980 when Alex Tilley, a man in his 40s, designed a boater hat that could do one simple task: stay on his head. He loved to sail but loathed the quality of what was available in the market. So he got to work. With the help of a couple friends, he designed a prototype with a fisherman’s knot to keep the hat steady. Some got wind of the invention and Tilley started selling the headpiece to buddies at the yacht club for $15.50 apiece, two dollars more than his costs. Before long, the sailing hobbyist grew that one hat into a multi-million dollar apparel business with a link to Canada as significant as basketball and the telephone.

I cannot tell you how many times I heard the response “Tilley? Oh, yeah, my dad is a big fan” while researching the company for this article. Everyone – and I mean everyone – talked about an older family member who still sports the O.G. bucket hat or how they’ve kept their grandfather’s in storage. As someone who didn’t grow up in Canada, it quickly became apparent that Tilley is both a piece of national and generational pride. But heritage can only get a brand so far.

The rise of fast-fashion chains, outdoor clothing retailers like MEC and Patagonia, as well as a desire from consumers to mix fashion with function, led to more competition than the company could bear. In 2015, after decades of building a travel and adventure clothing empire, Tilley sold the company to Re:Capital, the Canadian arm of U.K. private equity firm Hilco Capital. While a cash infusion helped the beleaguered brand get by, it wasn’t until Tilley caught the eye of fashion mogul Joe Mimran and his partner Frank Rocchetti that things really started to get interesting.

In an interview with the serial entrepreneur – best-known as the founder of Club Monaco and Joe Fresh – Mimran corroborated the theory that ​​Tilley is a much-loved brand in Canada. “There’s something about the Tilley brand. There’s always a family story. People still bring me their relative’s hat, like it memorialises their life. It’s very different from other fashion brands I’ve been involved with.”

At first Mimran and Rocchetti were simply passive investors. They later took on operational roles in 2020 after they convinced the management team to bring back the original bucket hat – which, to their surprise, had been discontinued – and refashioned it with a more modern, less wavy brim. They also introduced new millennial-inspired hues and updated the fabrics. “Tilley used to have three colours: khaki, khaki and khaki. So it was all very contrary to where the brand had been,” explains Mimran. The “Remastered T1 Bucket Hat” quickly became one of the best-selling products “and that’s when we got emotionally charged and into the business.”

Following T1’s success the duo built a team of product designers, developers and technical staff to take Tilley into more verticals.

Although, expansion into apparel beyond hats wasn’t entirely unchartered territory for the brand. Before its sale, Tilley’s portfolio had ballooned to hundreds of SKUs. It had a selection of shorts, shirts, vests, socks, even underwear with a secret pocket for storing valuables – all geared toward outdoor enthusiasts and travellers, with some of its hats carrying the brand’s famous “Guaranteed for Life” promise. But the challenge Mimran and Rocchetti faced was convincing a younger generation to see the brand as fashionable.

“At the very beginning, Joe, as the creative director said to the team, ‘We want to give the brand’s heritage a proper nod of respect, but if we don’t build this out and start attracting new customers and bring it to a more modern state, then we’re going to wake up and have a very small following over time,’” explains Rocchetti.

And therein lies the million-dollar question – how do you both modernise and pay homage to a brand’s old-school charm in a way that doesn’t alienate its loyal followers? You stick to what you know, says Rochetti. “We kept the principles to be aligned with the heritage brand, which is that the items should be enduring. They are made to last. They’re not fast fashion.” And you diversify, adds Mimran. “We’re taking the product lines and we’re seeing how we can segment the brand for various customers.”

Take, for instance, Tilley Tuff Workwear, a brand-new collection of engineered apparel, such as multi-pocket pants and weather-resistant jackets, which will be stocked at select RONA stores, as well as online. The new partnership allows the fashion brand to expand into the home improvement and construction space, which aligns with its expertise in outdoor gear.

There’s also Tilley Sport. Available in stores like Pebble Beach and Trendy Golf, and a mainstay at The Masters Tournament, the sport line has allowed the brand to access a throng of new buyers. And that extends to women, too. Tilley was previously dominated by men, and the decision to introduce colours and styles that appeal to the opposite sex has helped the brand go from an 80/20 divide to a more even 60/40 split. As for expanding the line: “Golf is our focus right now, but pickleball is a really big trend right as well. So a lot of the clothes are also very suitable for that, which is why we’ve opted for Tilly Sport, as opposed to just Tilly Golf,” notes Mimran.

The delicate dance between legacy and contemporary continues in the way in which Tilley’s products are marketed. “You’ll see in some of our photography, we’re not always using young models. There are people who have lived life in our campaigns,” says Rocchetti. But sometimes a brand needs to be overt in its intentions. It’s no coincidence the duo chose to open Tilley’s first store under their leadership along Toronto’s Ossington St. “We picked that very strategically – it wasn’t because of the shopping traffic pattern. It was more psychographic,” adds Mimran.

That Ossington St. store later went on to house a pop-up for Cafe Olimpico, a decades-old institution in Montreal that attracts coffee enthusiasts from around the globe. Pairing the two quintessential Canadian brands was a success on all counts, according to Mimran, who recalls there being line-ups for days while the cafe was in town for three weeks. “Anytime you can bring two heritage brands together, where each of them have street cred, it’s going to be a very successful partnership.”

Beyond the cafe collab, Tilley has also struck deals with forward-fashion shoe brands like New Era and Royal Albatross, Shiseido and its skincare line, paddle board company Beau Lake (of which Taxi’s Paul Lavoie is a founder), The Tragically Hip, and soon, the NBA. All of which lead to the ultimate goal of presenting a brand that’s more inclusive, accessible, relevant, modern.

If you’ve been in the business as long as Mimran and Rocchetti, you’ll know hard choices need to be made. “I can’t tell you the number of times people come to see Joe to ask for advice on how to expand into apparel. And he always says, ‘Don’t do it. You’re going to die doing it.’ And invariably, some of them stop. Most of them carry forward, and it becomes a very painful exercise.”

Their advice for those who do? Over deliver on value – and never underestimate the taste level of the consumer. “Offer them something that punches way above its own weight,” says Mimran. Sound advice from someone who brought modern style to the grocery aisle.