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Dad. Sometimes we call him Father when we're feeling extra respectful. But what we don't call him is dadster, because that's a cool name that would ignore the fact that he is so. Not. Cool. Nor is he interested in being cool. Asking your dad if he wants to be cool is like asking him if he wants to be up in da club – he's so beyond caring that he barely knows what you're talking about.

Now think of the brands most often associated with your dad, whether it's his running shoes, booze, car or cologne. None of them are known for their cool factor, either. They are practical and their sturdy dependability outlasts fluctuations in trends. Not too long ago, the list of these brands would register as lamer than a dad joke: New Balance, Old Spice, Canadian Club, Labatt 50. Over the last decade, however, each of them has enjoyed a resurgence in popularity, adopted by hipster fathers and style-conscious singletons thanks to their very dad-ness. But brands that try to shake their dusty reputation and take a shot at being hip are like a dad who hits the dance floor at a wedding – there are so many ways for things to go embarrassingly wrong.

"If the brief that I was given as a creative person was, 'Make people think their dad is cool,' I'd be terrified," says Todd Mackie, executive creative director at ad agency BBDO Canada. And yet, Mackie points out that several have pulled off that trick over the past few years.

Chrysler has been winning praise, and garnering millions of Youtube views, for its new marketing campaign to relaunch the Pacifica minivan – arguably the most lame parental vehicle of all time. "Is it possible for a minivan to be cool? I think so," says Marissa Hunter, director of brand advertising for FCA, Chrysler's parent company. Up until a couple of months ago, no one would have agreed with Hunter. But a spot featuring Jim Gaffigan (the endearingly slobby stand-up comic and father of five) talking about how the vehicle helps boost his "dad brand" makes it seem possible. However much Gaffigan goofs around in the commercials – he pretends to not know one of his kids' names in one spot – it's clear he's a caring father, both on and off screen. That authenticity is key to the success of the campaign, Hunter says. "He walks the real fatherhood walk every day."

Mackie's favourite dad-brand reimagination was a campaign for Canadian Club whisky in 2008. Capitalizing on the retro nostalgia of Mad Men, the "Damn right your dad drank it" campaign featured photos of men in the sixties and seventies, in situations including sitting with a women in his lap and fishing with buddies, above the cocksure lines "Your mom wasn't your dad's first" and "Your dad never tweezed anything," respectively. "Those ads were about repositioning how you think about your father," Mackie says. "You relate this [brand] to your dad and you don't think your dad's cool. That was a really smart tactic."

Even brands that opt not to play up the dad angle rarely distance themselves from it. Take, for example, New Balance, the most dad-like footwear this side of sporty sandals and black socks. Over the past several years, the brand has become a hipster favourite and the company has released one innovation after another, from a 3-D printed shoe to City Rivalry styles that via shoe design pit one sports-team-loving metropolis against another.

Chris Davis, the strategic business unit manager for New Balance's footwear, describes the company's target consumer as "metropolitan, globally minded, tech-savvy, ambitious and wears product to support her or his versatile lifestyle." In other words, as hip and youthful as customers of any smart sneaker company.

When I ask about New Balance's long-standing reputation as a dad shoe, Davis is unashamed. "New Balance is an organization proud of its legacy and tradition," he says. "In our world, classic is confident, authentic and sexy."

Ron Tite, chief executive officer of The Tite Group, a Toronto-based content-marketing firm, sees a similar attitude in rebranding campaigns for Old Spice, including both the "Man your man could smell like" and "Swagger" commercials. "Nowhere did they ever claim that Old Spice was 'New formula!' or 'Millennial scent!' or anything like that. They confidently embraced who they were," he says. Much like Canadian Club, they reference an earlier generation of guys that we romanticize more and more, Tite says. "The communications were like, 'This is the way your man should be' and they were hat-tipping to that nostalgia. Your man should be going back to these old values but in a totally contemporary way," Tite says.

And if Old Spice had come out with an ad campaign along the lines of "This ain't your dad's scent"? "We would have mocked it," Tite says. Dad brands that want to revitalize their reputations need to respect their pasts, never stray from who they are nor try to be cool. "When someone tries way too hard to do it," Tite says, "they get written off."

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