Timberland’s Most Iconic Boot Takes Things Up a Notch


The Timberland six-inch work boot occupies rarified space in contemporary fashion. It feels regional and global at once, and it now looks just as at home on runways as it does construction sites. This is thanks to countless 1990s New York rappers who were early to embrace the wheat-colored boot, weaving it into the fabric of influential hip-hop style. (Everyone from Biggie Smalls to Mobb Deep to Jay-Z to Kanye West has donned a pair.) The rugged boot eventually leaped into the fashion space, with designers and luxury labels paying homage to the style.

The shoe is undoubtedly a worldwide icon at this point but remains especially beloved in the Big Apple. You’ll see the unmissable silhouette everywhere: downtown, uptown, and in every other corner of the city. It makes perfect sense that Timberland has teamed up with Alife, a stalwart of New York streetwear since 1999, for a brand-new collaboration focused on the boot. Slightly more surprising? The fact that Alife has taken the classic Timberland to new heights—quite literally.

“Anyone that knows me can attest to the fact that I am in Timbs nine months out of the calendar year,” says Rob Cristofaro, Alife’s founder and chief creative officer. “The six-inch is the most iconic silhouette that Timberland has, hands down.” Needless to say, the significance of this particular boot was not lost on native New Yorker Cristofaro. In fact, this isn’t the first time the designer has added his stamp of approval to the boot—back in 2007, years before the collaboration frenzy would dominate the fashion space, Alife teamed up with Timberland to simply co-brand a pair of the iconic boots. This time around, Cristofaro knew he wanted to do something bigger.

It started with a high-concept idea: what if Timberland created a new silhouette that was simply an inch taller than the beloved original? A few years back, Cristofaro had already mocked up the “new” seven-inch boot, and it had been sitting in a folder on his computer ever since. Fast forward to 2019, when Cristofaro was introduced to a new director at Timberland by a close friend. He finally pitched the concept. After all the technical realities were ironed out, the boot ended up adding a total of an inch and a half to the original height. You’ll also see some nods to another New York-approved Timberland style, the Super Boot, which earned the nickname the” 40 Below” for its ability to stand up to bitterly cold weather. Cristofaro lovingly calls his boot the “20 Below,” as it splits the difference between the nine-inch Super Boot and the six-inch work boot.

Courtesy of Alife
Courtesy of Alife

Alife is known for bringing this unexpected, left-of-center aesthetic to projects, and this is no exception. (Just see the brand’s clog-with-sock Crocs). “Growing up a Native New Yorker, there are two shoes that represent New York like no other,” explains Cristofaro. “The first is the white-on-white Air Force 1s, and the other is the six-inch wheat Timbs. Period.” Cristofaro sees potential in this boot beyond a one-off collaboration, but instead that the silhouette can potentially become a mainstay in Timberland’s offering. Alife has managed to remix two revered boots into one eye-catching design that feels highly wearable, so the idea of that happening doesn’t feel that far-fetched. Time will tell if the silhouette lives on past this project. But Alife has been in the rough-and-tumble streetwear game for over 20 years—Cristofaro and crew have proven an eye for lasting design. And if anyone can design the next iconic Timberland, it’s undoubtedly a sharped-eyed New Yorker with a big idea.





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