Style That Works: How One Creative Rolls Up His Sleeves to Tell the Story of Workwear's Most Iconic Brand

Factory workers, finance types and fashion aficionados don’t typically agree on much—except for certain aspects of their style. Whether it’s a knit beanie, durable denim or an iconic duck fabric jacket, workwear has been an essential part of the American wardrobe since the 19th century, when it was originally marketed as tough, purpose-driven apparel for the booming American labor force. Today, it permeates every facet of American fashion, and one brand has consistently been at the forefront.In 1889, businessman Hamilton Carhartt had a failing apparel company that he marketed to the average American worker. When the business was on the brink of collapse, he desperately asked rail workers what kind of apparel they’d find most useful.What resulted wasn’t just the iconic bib denim overalls—a workwear icon that’s still a staple of the Carhartt line. It emerged as a brand that defined an entire category of tough, functional apparel all over the world.“Hamilton had a great voice, and he was an excellent marketer,” says Brian Bennett, the brand’s creative director, who oversees branding, advertising and product development. “Once he created a product that worked so well, the brand really marketed itself for years through the clothes themselves, and they took on the lives of the people who wore them.”By the early 20th century, that group also included the military. The brand had several factories in the U.S., Canada and the U.K., and when World War I broke out, those same factories were used to create uniforms for soldiers. Later, Carhartt would produce denim for the U.S. Navy and women’s uniforms in World War II.Today, Bennett is the modern-day version of Hamilton, telling the brand’s stories through the lens of his customers’ tough-as-nails work ethic. His role has evolved over the years, as the brand has reached beyond its American working-class appeal. “I’m a copywriter by trade, but what was so exciting was finding the brand’s story—its central concept—and then developing not just a TV commercial, as I’d done in the past, but the marketing plan, hang tags, the look and feel of the retail stores—everything,” he says. Bennett’s work in the advertising world has earned him a number of prestigious awards, including a Clio, an Effie and even a Cannes Lion, with a list of clients that includes Nike and Corona.When the opportunity to steer Carhartt’s creative side came up five years ago, he was hesitant to uproot his family and move to the company’s headquarters in Dearborn, Michigan, just outside of Detroit. “I had no desire,” he says plainly. “But then I met our owner, Mark Valade—Hamilton’s great-grandson. He told me his story as a fourth-generation Carhartt, and I realized this was actually my dream: to build a creative department for a128-year-old brand that really hadn’t told its story since the early 1900s.”Even after Hamilton Carhartt passed away in 1937, Americans remained fiercely loyal to the brand. Theproducts are still made in America, with facilities in Detroit, Kentucky and Tennessee that employ some2,000 workers who produce more than 7 million garments every year. Some of the iconic pieces to come out of those factories include the double-front dungaree, introduced in 1932, and the Active Jac hoodie from 1976—still a top-seller. It’s made of Carhartt’s iconic duck fabric, a tough, water-repellant cotton canvas that debuted in 1929 and is still sold today, largely unchanged from the original."Carhartt has always been that go-to heritage brand for hardworking American guys,” says Jennifer Ryan Jones, a veteran menswear editor whose work has appeared in Playboy, Men’s Health and The Manual, among others. “When I hear the name, I think of the iconic Weathered Duck Detroit Jacket in that signature golden-brown color.”While the clothes remained the same, Carhartt’s hometown of Detroit did change over the next century—drastically. Despite its economic downfall, Bennett says the city still surprises him. “Today, when you look at the city from the outside, you can’t tell how beautiful it is on the inside,” he says. “Especially because there are so many people in Michigan who know how to make and build things. The auto industry boomed here because Detroit was a cheap manufacturing place, but now you can come here and meet a different small business owner every day. You’d be here for months.”With the inspiring stories of people making things in Michigan, he hasn’t had to look far for the subjects of his advertising campaigns. “I don’t like marketing fluff,” says Bennett. “I want the stories I tell to be real—never fabricated. But I don’t want to do ads about people digging ditches, either. I want to go deeper to see what inspires them to keep going and how we can help them accomplish their goals.” To do this, Bennett seeks out the places hefinds to be quintessentially Detroit, like Miller’s Bar in Dearborn, Two James Spirits’ tasting room in Southwestern Detroit and the iconic Michigan Central Station, which was once a bustling train depot.Located in Corktown, one of the city’s oldest neighborhoods, it now stands as a towering relic of Detroit’s industrial might. Today, Bennett and his team are speaking to a much larger audience than when the brand first started, especially considering that every American wears workwear in one form or another. “The whole categoryhas been redefining what we wear for centuries,” says Jones. “It’s always been present in menswear.”In the ’70s and ’80s, Carhartt took on a new life, becoming an anti-fashion icon on the punk scene. In the ’90s, grunge adopted the trend, and soon other subcultures followed suit.“What’s amazing is that Carhartt is also considered a legit streetwear brand since it was anointed by hip-hop culture in the early ’90s,” says Jones. Artists like Dr. Dre, Nas and House of Pain became unofficial ambassadorsfor the brand, wearing the clothes—especially the duck jacket—in public and in music videos.Today, hipsters have also adopted the brand. As marketing chief Tony Ambroza told The Guardian, “They seem to like what we stand for, and that they can’t find our clothes at mass-market retailers.” The brand brilliantly stoked that fire by launching a craft beer with New Holland Brewing. You’ll also find the familiar Carhartt beanies liningthe runways of New York Fashion Week on men and women alike. And although the brand didn’t try to reach the high-fashion crowd, it did tap into a more urban consumer with the launch of Carhartt Work in Progress in Europe in 1989, as the line adapts the brand’s core pieces for a more fashion-driven take on workwear. It has also  generated plenty of buzz by collaborating with fashion brands like A.P.C., Vans and Junya Watanabe.However, Bennett is emphatic that traditional workwear is still the brand’s focus. “I think the trick is to be relatable and honest without losing who you are,” he says. It’s a theory that has helped Carhartt stand the test of time. “The fact that Carhartt is still around today, relevant as ever, is a testament to the quality of the clothes,” says Jones. “If you’re busting your tail roofing, doing construction or cutting down trees, you’re not spending that hard-earned paycheck on clothes that don’t wear well. Carhartt holds up and gets the job done.”Even though Carhartt always relies on its core collection, Bennett says he wants to bring innovation to the brand. “I want to enhance worker vitality with our products and become essential to their work day—essentially what FitBit has done for the athlete,” he says. “We’re going to go deeper into helping our customers’ well-being. It’s scary to figure out how to innovate and tell stories like that, but I love that we have that challenge in front of us.”This feature on Brian Bennett, Carhartt's creative director, appeared in ALIVE's 2017 Issue 2, available in a digital edition.Photography by Attilio D'Agostino.