The nation's most iconic brands all have staying power, but few can stick it out five generations like Carhartt, the made-in-America family business that's popular among everyone from roughnecks to Rihanna.

"Few brands have been able to stand the test of time through decades of evolving consumer behaviors and at times an even more volatile economy," says Krista Corrigan, a retail analyst at New York City-based Edited. "Carhartt has not only managed to remain relevant, but has adapted and thrived in the changing environment.?"

The story behind how this chameleon of a brand, which was doing an estimated $630 million in revenue in 2014, managed this feat is as much a testament to the value of craftsmanship and conservation as it is strategy and innovation. 

A funny thing happened in 1992 ...

At the time, Carhartt was a little more-than-100-year-old blue-collar workwear brand founded by the Detroit horse-and-wagon salesman Hamilton "Ham" Carhartt. Its signature product, even more popular than its original sturdy canvas overalls, was a jacket: the Weathered Duck Detroit. The company sold it in mustard or navy blue 12-ounce cotton canvas, dubbed "duck," with triple-stitched seams and metal rivets. It hit at the waist to "keep your tool belt in mind."

The jacket for a century had been a favorite outerwear of hunters, railway workers, and  oil riggers. Then, in 1992, it showed up in the video for "Jump Around" by House of Pain.

It was a shift, but not entirely diametric. The jacket had already made a more subtle entrée into city streetwear. Drug dealers had by the late 1980s discovered its utility and sturdiness. "They needed to keep warm and they needed to carry a lot of stuff," Steven J. Rapiel, the New York City salesman for Carhartt, remarked to The New York Times. "Then the kids saw these guys on the street, and it became the hip thing to wear." By 1990, Tommy Boy Records, the hip-hop label, decided to use the popular jacket as a promotion, giving 800 of them to "taste makers." "It took off immediately," Monica Lynch, Tommy Boy's president, told the Times. Before long, the label signed the hip-hop group House of Pain, and, suddenly, the gear favored by large-animal veterinarians was jumping around.

It wasn't only the appropriation by drug dealers and rappers that led to the cultural explosion of what had been, essentially, a barn jacket. In 1989, Swiss denim specialists and designers Edwin and Salomee Faeh struck a licensing deal with Carhartt in the United States to tailor the classic, sturdy clothes to a more streamlined skater aesthetic, and take it to Europe. What resulted was a line, Carhartt Work in Progress, or WIP, not just tailor-made for the city streets but also for editorial packages in all the glossy fashion and culture mags.

Back in America, some of that European luster rubbed off on the brand. Carhartt didn't shy from it; instead it worked with fashion's elite, executing collaborations with brands such as A.P.C. and Adam Kimmel. The appeal couldn't have been more tailor-made if Hamilton Carhartt had sewn it himself: By the 2010s, a fresh wave of Brooklyn hipsters, whom some dubbed "lumbersexuals," were sporting Carhartt beanies and jackets. Skaters and hip-hop heads hadn't given up on it. Perhaps unsurprisingly, it also got big in Japan. There's also a women's line. 

All the while, the steady, classic brand never lost its blue-collar appeal. It was, in this way, handy to politicians: Everyone from Sarah Palin to Barack Obama has worn Carhartt prominently, at rallies and campaign events. The blue-collar appeal is so strong that Esquire wrote: "These jackets are everything the American man aspires to be. They're tough as hell. They'll keep you extremely warm in the winter. They look good when dirty ... They're unpretentious, masculine, and completely non-BS."

"Honest value for an honest dollar"

These qualities can be traced back to Hamilton. Around the turn of the 20th century, Ham Carhartt began hand-sewing overalls after getting requests from railway workers. He used a half-horsepower electric sewing machine in a small Detroit loft--and by 1910 he'd grown his enterprise to a company that operated cotton mills in South Carolina and Georgia and four sewing facilities across the U.S.

A distinctly hard-working vibe was infused into the whole operation by its founder. "Honest value for an honest dollar" was the motto. But after the company nearly crumbled during the 1929 stock-market collapse and subsequent depression, Hamilton's son Wylie became president in 1937 and debuted new outdoor lines of hunting wear. Wylie Carhartt's daughter, Gretchen, married Robert Valade--who took over the company's helm in 1959. He modernized Carhartt's production facilities, and began a private-label business, creating products specifically for department stores. The brand continued to grow, and gained popularity with construction and outdoor workers, who found the tough outerwear held up to harsh conditions. Word of mouth led to more sales, with help from major construction projects across North America, such as the construction of the trans-Alaska Pipeline, which commenced in 1975.

In 1996, Hamilton's great grandson, Mark Valade, became president of Carhartt. Having grown up in the family business, he established new operations in Europe and a global e-commerce business. He transitioned to CEO in 2013, and in a sweep opened up dozens of Carhartt retail stores and a women's line--fully embracing its ability to cross borders, demographics, and tastes. This is how Matthew McConaughey dons a sand-colored Duck Detroit jacket throughout the 2014 film Interstellar and by 2018 New York magazine ponders: "Why can't I walk five blocks without seeing a Carhartt beanie?"

To be sure, most family businesses struggle with succession planning; 70 percent don't make it to even a second generation, according to Margarita Tsoutsoura, the John and Dyan Smith Professor of Management and Family Business at Cornell's SC Johnson College of Business. However, at Carhartt, which is now onto its fifth generation--one family member is a web developer, another is in marketing--every generational shift has seemed to make it stronger, and that's helped further diversify its fan base. 

Perhaps some of the strength comes from the long-term view family-run businesses tend to take, says Carrie Hall, who leads Ernst & Young's network of family business professionals. A massive study of large family-run businesses the group conducted showed that the ability to make decisions based on a long view afforded such businesses many benefits.

"They don't worry about what analysts think, or focus on making themselves look attractive to investors," Hall says. "They are adamant that they are going to build something as good stewards of passing on their work to the next generation."