THE JOURNAL
In 1973, Massachusetts bootmaker Nathan Swartz injection-moulded a waterproof leather boot for New England construction sites and forestry crews. Nobody involved in the making of that Timberland eight-inch boot (the classic six-inch would be released three years later) could have predicted that this piece of unglamorous utility would become one of the most quietly influential objects in street style. It was claimed, in turn, by Milanese paninari, Bronx MCs, Compton rappers and London ravers, each group shaping its meaning to fit their own cultural code.
A “paninaro” wearing Timberland boots in Piazza San Babila, Milan, Italy, 1987. Photograph by Egizio Fabbrici/Mondadori via Getty Images
One of the boot’s earliest detours from the job site was in Italy. In early 1980s Milan, a bunch of teenagers started hanging around city spots like Burghy and Il Panino (which gave them the name paninari), mixing up American Ivy League dress and outdoor brands with European sportswear.
Timberland boots, worn with rolled-up jeans and bright puffer jackets, were a hit precisely because they looked foreign and went against the rigorous traditions of a city otherwise built on tailoring. It wasn’t so much about footwear, but showing they had access to American gear and couldn’t care less about the local dress code.
The Notorious BIG aka Biggie Smalls performing at KMEL Summer Jam 1995 at Shoreline Amphitheatre in Mountain View, California, 11 August 1995. Photograph by Tim Mosenfelder/ImageDirect
Across the ocean, another transformation was underway. By the mid-1980s, Timberlands had taken over the streets of New York, where hip-hop culture was busy reassigning meaning to workwear brands. The boot’s honey nubuck came to symbolise an unspoken style authority – anyone from Boot Camp Clik to The Notorious BIG, Wu-Tang Clan and DMX helped cement the association through the early 1990s (with the latter even claiming he owned 1,500 pairs over the years).
In Los Angeles and Compton, rap culture of the same years had its very own regional footwear hierarchy, but Timberland found its way in through a similar instinct: taking a boot designed for cold, wet labour and repurposing it as a marker of resilience and self-reliance, regardless of climate. In that context, Timbs just needed to look like they could survive anything.
R&B group Intro in New York City, 10 July 1992. Photograph by Al Pereira/Getty Images/Michael Ochs Archives
By the 1990s and into the UK garage and jungle scenes, the brand had gone fully global, adopted by ravers and MCs who valued the same qualities that had first appealed to New England construction workers two decades earlier: durability, weight and a certain refusal to be subtle.
More recently, Timberland has enjoyed somewhat of a resurgence thanks to collaborations with the likes of Aimé Leon Dore, Our Legacy Work Shop, JJJJound and Beams, among others. Luxury labels have put their spin on it, too – in 2025, Jacquemus reworked the three-eye lug boat shoe in banana yellow, followed by a second colourway in light blue this year.
What ties these subcultures and brands together isn’t a shared aesthetic, but a shared instinct to take a shoe built for function and pack it with meaning that its original designers never thought of. Not many shoes can claim to have undergone so many reinventions and walk on as culturally relevant as ever.