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Shoppers peruse the Fluevog headquarters in Vancouver on March 9. The boutique retailer is among Canada’s most distinctive. It has two dozen stores throughout North America and in late March is set to open its first overseas, in Amsterdam.BEN NELMS

For John Fluevog, the iconoclast designer of his namesake footwear, shoes have always been about entertainment.

Walk into the Fluevog flagship store on Water Street in Vancouver and the shoes on display feel like a party, a kaleidoscope of colours and styles. They are arrayed on three long beams of brown English oak, the wood from trees two centuries old. The shoes, the company advertises, are "unique soles for unique souls." Fluevog fans include everyone from Beyoncé to Jack White.

On the mezzanine – under a glass atrium in a space between two old brick buildings – stands Mr. Fluevog, a couple months before his 70th birthday. From this perch he oversees what he calls his "little art project." He designs some 75 shoes a year. He's wearing a new pair set for release this fall. They are a mash-up of formal and casual, a black leather dress shoe on a rubber serrated sole of aqua green, white and black. The idea emerged a few months ago as he connected two disparate pieces.

"We were fooling around here in the office," Mr. Fluevog said. "I go, 'These look crazy. Nobody's doing anything like this. I'd wear those.' And I do."

This is the embodiment of the company's ethos – "embrace peculiarity" – one Mr. Fluevog has forged over nearly a half century in the shoe business. The company today, however, is at a crossroads, as John Fluevog Boots and Shoes Inc. readies for life after John Fluevog.

The boutique retailer is among Canada's most distinctive. It has two dozen stores throughout North America and in late March is set to open its first overseas, in Amsterdam. There is ambition to grow to as many as 100 stores. At the same time Fluevog has cuts ties with Amazon.com Inc. and other wholesalers, to do almost all of its business in its own stores and website. It's an emerging trend in retail to exert as much control over one's own brand as possible.

Adrian Fluevog, the company's chief executive and John's 36-year-old son, said they wrestled with the Amazon decision. It came down to one question: "Is it good for the brand to be there?" They decided two years ago it wasn't. "Our brand didn't feel special on Amazon," he said.

Sales didn't falter and 2017 was a record year. Adrian has helped already lead expansion to 25 stores from 10 since 2010 and he's poised for more.

"I feel like we're just beginning," Adrian said. "We've got something special. John has built the DNA. Let's run with this. Let's have some fun."

Vancouver has long been a font of Canadian retail that has garnered a devoted following, including names such as Aritzia, Lululemon and MEC. The roots of Fluevog stretch back to 1970 but it was the 1980s when Fluevog as it exists today began. John, in his mid-30s, started to design shoes, and put his name on the store. He had no formal design training and his confidence had taken time to coalesce.

"You need boldness," John said. "It's quite a step. It's not that easy." He trusted his instincts. "I did whatever wacky things that came into my brain – and they actually sold."

Fluevog expanded to Seattle in 1985, and Boston, Toronto and New York soon after. An endorsement came in 1991, when Madonna wore Fluevogs in her film Truth or Dare: a pair of Munsters – black platforms with a big silver buckle and a pyramid heel.

Around 2000, the company struggled, as it buckled under the weight of too much inventory, when sales to U.S. boutiques faltered.

"I was on an old energy," John said. He refocused on his own stores and in 2001 he introduced a popular new design: a three-inch heel in the shape of an hourglass, dubbed the Mini. Expansion was on again by 2004 with a store in Los Angeles.

In 2010 came a demarcation between past and future. The Museum of Vancouver staged a design retrospective and Fast Company, with Mark Zuckerberg on its magazine cover, included Fluevog on a list of the world's most innovative companies. There were 10 Fluevog stores at the time. Adrian had rejoined the firm after a previous stint and he brought a new business savvy. The company doubled its stores in about four years.

Around the same time, John was struck by leukemia. "I had an encounter with my mortality," he said. "I had to let everything go."

It sharpened his thinking of Fluevog without John Fluevog. He beat the cancer and he beat a recurrence several years later.

Succession planning has happened on several fronts. Adrian became CEO last June. John has started a corporate advisory board and he also has specialists to advise him on legal questions and psychological ones – the personal nature of family businesses.

Michelle Osry, a partner at Deloitte LLP in Vancouver and expert in succession matters, said succession too often focus on money and tax planning. The real questions are about shared goals and the business's direction. Ms. Osry cited Hermès SA, the French luxury-goods maker founded in 1837 by Thierry Hermès. The Hermès family constitution speaks of family members being stewards, rather than inheritors of wealth.

Today, as John turns 70 in May, he is semi-retired – but has no plan to retire. He has his eight-by-eight inch Flexi-Sketch book on hand, where his drawings range from concepts to more detailed ideas.

"I have more time to dream," he said.

The company's design process has evolved. John produces most of the foundational designs, but the final results are a team effort.

"He's letting go, more and more," said Arabella Barros, head of the company's design department. "He trusts the team a lot more. He's letting us go in different directions."

To Adrian, his dad's name will always be on the stores and the shoes, but the company has grown beyond a single name.

"Fluevog has its own energy," Adrian said. "You can't replace John but the company is strong enough to keep going."

Then there is the challenge of managing growth, a tricky one for a company such as Fluevog, said Doug Stephens, president of consultancy Retail Prophet.

"If you're a brand that's staked its reputation on quirky, kind of bizarre, on not being a commodity, on being unique – almost aloof – you have to be careful you don't overdistribute," Mr. Stephens said.

As Fluevog expands, an important factor is its work to control its brand, like cutting ties with Amazon. Last fall, Nike Inc. made a similar move when it decided it would pin its future on 40 essential retailers, including Amazon – a fraction of the 30,000 retailers that sell Nike products. Trevor Edwards, a top Nike executive, declared: "Mediocre retail won't survive."

"More and more brands are taking their destiny into their own hands," Mr. Stephens said.

John Fluevog has previously imagined global expansion. A quarter century ago, there was a brief but ill-fated attempt at wholesaling in Europe. Now, as a Fluevog opens in Amsterdam, the founder is letting go.

“I’ve always had the sense that this could grow, that it could be a global company. We’ve never really gotten there,” John said. “As I think about where I’m at in my life, if the company is going to carry on, I need to be able to pass it on, so that the essence of the brand stays the same, but it doesn’t necessarily need to be me.”

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