The iconic work- and streetwear accessory is an American wardrobe staple beloved by Naomi Campbell, Emily Ratajkowski, Teyana Taylor, and hip-hop legends.
Trends come and go, but classics are forever. With the Anatomy of an Investment Piece, we highlight the timeless styles you need in your wardrobe and break down what exactly makes them worth buying. Whether it’s a forever bag, wear-everywhere coat, or footwear staple, these fashion pieces are icons in the making.
As a brand, Timberland slays the house down boots. In other words, it’s timeless, beloved, an instantly recognizable legend. Just take a look at the stars of its latest aptly-titled “Iconic” campaign, which includes supermodel Naomi Campbell; rising, genre-defying singer-songwriter Teddy Swims; designer-artist Slawn, and Kai-Isaiah Jamal, the multi-hyphenate non-binary and trans visibility activist from the U.K. In the black-and-white portfolio, lensed by Jamie Morgan, the diverse roster of performers pose individually across energetic, empowering shots that highlight the brand’s secret ingredient for the past 51 years, the Original Yellow Boots.
Originally introduced to the world in 1973 as the Boston-based Abington Shoe Company’s Original 8-inch Timberland Boot (more on that later), Timberland boots were made to endure the harsh, cold, wet weather conditions Northeastern outdoor workers faced.
The Original Yellow Boot—as it's informally referred to because of its unique wheat Nubuck color—is as American as apple pie, fireworks on the Fourth of July, Calvin Klein underwear, or a Starbucks Pumpkin Spice Latte on the first day of fall. It's as gritty and masculine as it is sleek and feminine, and the “Iconic” campaign, released a year after Timberland celebrated its 50th anniversary, mirrors the Yellow Boot's elegant staying power.
“As the product continued to take on new meaning, it evolved into a symbol of inclusivity and self-expression, resonating with the next generation who value individuality and purpose,” says Maisie Willoughhby, Timberland’s Chief Marketing Officer and the heck of a good time over lobster rolls, a seafood boil, and Old Bay seasoning at dinnertime in New England.
In July, I had the privilege of visiting Timberland’s headquarters in Stratham, New Hampshire, and spent time with Willoughhby and her team discussing, well, boots. “The Yellow Boot is no longer just footwear; it’s a cultural icon that adapts and thrives, reflecting on the ever-changing landscape of fashion, identity, and social impact.”
But how did this icon come to be, and what makes it so particularly special?
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The History
In 1973, Before Timberland was officially Timberland, craftsman Nathan Swartz (with the help of his son, Sidney) developed and introduced an innovative waterproof design called the Original Timberland 8-inch Boot, released by the Abington Shoe Company built in part by the Swartz patriarch. Swartz and his team of shoemakers used direct-injection and direct-attach technology to bond the outsole to the upper-sole and add silicone to the leather of the boots, essentially sealing the bottom to create the very first legitimately waterproof boot.
“There were no designers at the time,” says Alex Dardinski, a senior designer at Timberland who's worked at the brand for 25 years. “These were really just shoemakers that were focused on the craft and this new technology. The folklore around [the Original Yellow Boot] is that there was leftover leather in the [wheat] color and they used it; it became legend after Timberland took ownership of that color.”
Because of the original boot’s success, a 6-inch version was released three years later, and the company eventually rebranded as Timberland in 1978, initially focused on creating rugged work boots for the labor force long before becoming the footwear, accessories, and apparel behemoth it is today.
“Today’s boot is remarkably similar to the original product—we’re actually pretty reluctant to make changes to it,” Dardinski says, teeing up an explanation of the evolution of Yellow Boot consumer. “It was originally adopted by tradespeople that were working in harsh conditions, and then it was adopted by people who were like, Hey, I want to go hiking and I want my feet not to get soaked."
He continues, "And then it was adopted by New England college kids commuting to class in the snow. Then, it was Italians wanting a little piece of Americana, or British ravers out at a rave. And then hip-hop obviously adopted it in the biggest way in the ‘90s; that made them feel badass and as big, indestructible of a product as ever.”
Dardinski explains Timberland’s design team riffs on the Yellow Boots by reissuing or remastering creative, collaborative versions made with updated materials and surprising blends of color. His team's M.O.? Don't veer too far from the OG boot’s DNA. “You can’t make an iconic product, you just can’t,” Dardinski says. “The culture does that for you.”
The Craftsmanship
Timberland boots are meant to last and resist wear and tear. As I witnessed at Timberland HQ while touring The Shed (the brand’s design lab), Nubuck leathers are cut and sewn together before hi-tech injection molding machines add silicone that help the boots stand up against water. Rustproof eyelets are used and paired with strong Taslan laces. Four rows of stitches work to prevent rotting and mildew. For comfort, the soles use anti-fatigue technology with a geometric cone that absorbs shock and literally feels good on your feet.
And then there’s the aesthetic. In addition to a neutral wheat color that goes with everything, plus a sexy, double foam-padded leather collar around the ankle, Timberland Yellow Boots are each emblazoned with a tree logo, a nod to the brand’s outdoors heritage. .
“The boot really started as a tool, an innovation for blue collar workers, and now it’s 51 years old and in high-fashion shows,” Dardinski says. “It shows the rise of streetwear culture drawn from these iconic pieces that were really meant to be functional. It’s incredible to see the transformation in the past 50 years of how luxury has really changed.”
The Appeal
This year, Louis Vuitton introduced a fall/winter 2024 men’s workwear capsule collection with Timberland, marrying both brands' proclivity for utility, fashion, craftsmanship, and cultural cache. Select items in the Pharrell Williams–designed capsule include his interpretation of the Yellow Boot, a bling-ified version priced at $2,850.
“For Timberland, we seek partners who share our passion for innovation, premium materials, quality craftsmanship, and cultural relevance," Willoughhby says. "Working with LV takes all of this to the next level—they are first-in-class when it comes to designing beautiful products that withstand the test of time." Timberland has previously collaborated with Supreme, Jimmy Choo, Wales Bonner, and White Mountaneering.
The brand’s cultural relevance didn’t appear out of thin air, though. Willoughhby describes the Yellow Boot as “a symbol of New York streetwear” and “one of the long-lasting fashion symbols of hip-hop culture” still adopted by “new communities and generations globally.” And she’s not wrong.
In the ‘80s, Italy’s “paninaro” style youthquake found Italians dressing in their interpretations of how Americans dress, tying up their Timberlands to achieve the look the same way Japanese fashion lovers did in Tokyo’s Harajuku district, where hyper-expressive fashion remains celebrated. In the ‘90s, rappers and musicians like Nas, Tupac, Aaliyah, and Biggie regularly wore Timberland boots onstage and in music videos, solidifying the brand as a celebrity-approved favorite. Today they're worn by the likes of Teyana Taylor, Emily Ratajkowski, and Rihanna.
The Timberland Yellow 6-inch Boot retails for $198, a reasonable price for a long lasting accessory revered by the general population and the luxury fashion world. Reflecting on the “Iconic” campaign, Willoughhby underscores why the brand is synonymous with that oft-overused word, and just how much Timberland has pervaded culture for decades: “The campaign celebrates the individuals who continue to push boundaries and define what it means to be truly iconic.”