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Joe Mimran, co-owner of Tilley, at the brand's Toronto store, on Feb. 18.Christopher Katsarov/The Globe and Mail

At the Tilley store in Toronto, there are plenty of hats on display: bucket hats in several hues, down-filled styles for chilly months, “Aviators” with sherpa-lined ear flaps. But if you’re looking for that Tilley hat – the dun-coloured model with the wide, flat brim and snap-up sides – you may need to ask for some assistance.

“They’re not on display, but we still have them in the store in a multitude of colours,” Tilley’s co-owner, Canadian retail veteran Joe Mimran, says of the older designs. “When a customer comes in, they know what they’re asking for.”

Those loyal fans – sailors, birdwatchers, travellers of a certain age – have kept Tilley Endurables Inc. in business for more than 40 years. Tilley’s new owners don’t want to alienate this crucial group, but they also know the future of the brand relies on drawing in new customers.

“We want to take the heritage of the company and we just want to bring it up to date,” Mr. Mimran says.

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Mr. Mimran says he was drawn to Tilley because he wants to revitalize a Canadian label that built a significant presence over the years.Christopher Katsarov/The Globe and Mail

Mr. Mimran brings with him years of experience in apparel retail, having built Club Monaco before selling it to Ralph Lauren in 1999, as well as creating the Joe Fresh cheap-chic line for grocery giant Loblaw Cos. Ltd. Formerly a regular on CBC’s business reality show Dragons’ Den, Mr. Mimran has also invested in Canadian brands such as pantyhose-disruptor Sheertex and online housewares retailer Goodee.

Tilley got its start in 1980, when founder Alex Tilley, an avid sailor, wanted a better hat to wear on the water. He designed his own and began by selling it at boat shows. Its popularity grew, winning over hunters, hikers and fishing enthusiasts. The advertising focused on the product’s lifetime warranty and durability, boasting that a Tilley hat had travelled through an elephant’s digestive system – thrice – and emerged in one piece.

Despite attracting stalwart fans, Tilley’s sales began slipping as it faced competition from both fast-fashion chains and outdoor retailers such as MEC and North Face. In 2015, the business was acquired for an undisclosed sum by Re:Capital, the Canadian arm of British private equity firm Hilco Capital, which specializes in turning around distressed companies.

Re:Capital more than doubled Tilley’s wholesale business, taking it from selling in 2,500 stores in 2015, to roughly 7,000 in 2017 – including locations in Canada, the U.S., Britain, Australia, Europe, Japan, Singapore and Taiwan.

But the brand had become tired and was losing money, Mr. Mimran says. When the pandemic hit, many of the retailers that sold Tilley products faced a crisis. The equity group considered winding the company down. Instead, Mr. Mimran and his partner Frank Rocchetti stepped in. They had first invested in Tilley in 2018, and took a majority stake in 2020, deciding to run the business. Mr. Mimran’s investment firm Gibraltar & Co. has a stake in Tilley as well.

Mr. Mimran’s goal is to convince a new generation of customers that Tilley is chic. The fashion resurgence of the bucket hat helps: Tilley’s very first hat was a rugged version of this design. (That was before the wider brimmed “Airflo” design took over in the 2000s, eventually accounting for the majority of its sales.) Mr. Mimran’s team gave the “T1″ bucket a makeover, designing a brim that was less wavy, very slightly increasing the height and introducing new colours – cobalt, yellow, a distinctly millennial pink – and fabrics, such as corduroy and recycled nylon.

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Mr. Mimran greets customers at the Tilley store in Toronto. His goal is to convince a new generation of customers that Tilley is chic.Christopher Katsarov/The Globe and Mail

Mr. Mimran wants to upend what he calls Tilley’s “one-note business” that relied heavily on that single wide-brimmed hat, and is expanding into apparel. Walking around the store, he holds out the sleeve of a cashmere top, and talks up the “hand feel” of the polar fleece or the fill power of the down coats.

He is interrupted, once or twice. Fellow former Dragons’ Den judge Michael Wekerle, who is visiting the store, cannot resist getting in on the sales pitch. He occasionally stampedes into the conversation to praise his friend’s fashion and business sense, or to bellow, “How can you not buy clothes from Joe Mimran?” His magpie attention then flits back to a sales associate, as he declares that he wants a bucket hat in every colour.

The one-man confidence band notwithstanding, Tilley has to win over a broader customer base. But it’s not the first time the brand has tried to branch out. In 2017, Tilley introduced new styles such as wool beanies, baseball hats and newsboy caps in a bid to woo younger outdoor enthusiasts – exactly what Mr. Mimran is now trying to do. So why should it work this time?

“They ‘third-partied’ the apparel,” Mr. Mimran says of the previous owners, explaining that they hired consultants, and the products were not successful. (Previous Tilley executives declined or did not respond to requests for interviews for this article.) “Apparel is obviously something that we know how to do, so we took it all in-house and we really expanded the entire design team, the product development team, the sourcing team.”

The company has held on to its 45,000-square-foot manufacturing and distribution facility in Toronto, where many of the hats are still made – though it now also sources from China, Portugal, Italy and Japan.

It has also dramatically expanded its e-commerce site, which now accounts for roughly one-third of its business. The brand has gone from $20-million in annual sales to roughly $45-million in just a couple of years, and Mr. Mimran says it is now profitable. It has updated the brick-and-mortar presence, too, closing down one “old and tired” store, and opening the new location in Toronto late last year. A pop-up shop at the city’s high-end Yorkdale mall is also acting as a billboard for the brand overhaul.

The next step is to begin selling the clothing more widely through wholesale partnerships; Tilley already sells its hats to roughly 3,000 retail outlets across Canada, the U.S., Britain and Australia.

“There’s an opportunity for Tilley, because it’s known for its quality and durability, but it needed an infusion of fashion – reinvigorating the brand so that it’s not known as your grandfather’s hat,” says Lisa Hutcheson, managing partner with retail consultancy J.C. Williams Group.

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The brand has more than doubled its annual sales to roughly $45-million in just a couple of years, and Mr. Mimran says it is now profitable.Christopher Katsarov/The Globe and Mail

But like other clothing retailers, Tilley will have to grapple with waning consumer confidence. While Tilley is hardly at the luxury tier, it is depending on customers who feel inclined to spend more than $200 on a plaid flannel shirt, for example. In January, a DBRS Morningstar report predicted that companies selling discretionary goods would generally find themselves under pressure “as consumer purchasing power continues to be eroded by high inflation and elevated interest rates, and pandemic-related pent-up demand wanes.” It included apparel among the categories that could expect softening demand this year.

Still, there are signs that a wider audience is finding the brand: While its website has reviews from loyal fans, including one pleased with the warranty on a 12-year-old hat, another seemingly younger reviewer features five fire emojis.

Mr. Mimran says he was drawn to Tilley as his next retail act because he wants to revitalize a Canadian label that built a significant presence over the years.

“It was a super interesting brand. I remember Tilley,” he says. “I feel it has huge potential. The customer will tell me if I’m right or wrong.”

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