Timberland hardly needs an introduction. The brand has made one of the most popular boots ever—the six-inch, obviously—and has even churned out incredible collaborations with streetwear heavyweights like Supreme and Stussy. It's no easy feat to stay in business for 40 years—and even harder, to stay relevant—yet Timberland has achieved just that. 

We recently visited the company's headquarters in Stratham, NH to get a preview of upcoming collections and sat down with creative director Chris Pawlus, who talked about Timberland's collaborations, how it's been able to stay successful, and what he thinks about the brand's relevance in hip-hop.

Interview by Karizza Sanchez

Timberland's collaborations have always hit a mark with our readers—especially projects with Supreme, Stussy, and Opening Ceremony. How did those come about?  
I think the successful relationships are because they're relationships, they're partnerships. And I think some of the better ideas are iriterative—one idea connects with another idea over time. There's this evolving relationship where you can try things you were maybe reluctant to try at first but then the time's right to try it now. I think that comes with trusting one another, but also recognizing what trends are right for both collaborators in the sense that there are certain things that Timberland couldn't do by itself, but in the realm of collaborations becomes okay to try.

Sometimes maybe there are experiments that, I should say, the outcome is greater than one expected, and then sometimes there's a little bit of an anticipation for a delayed response—What do the consumers think about it? And then hearing the feedback on theblogs and hearing how people respond to it is really important. I guess what I'm getting at is the consumer and their voice is really the goal of the collaborations. I think the collaborations gain that attention, too. It invites a conversation. 

The one that we have with 10.Deep, for example, the Nomad boot, we're seeing a rising trend in '90s hiking silhouettes and that seems to be resonating with a lot of our core consumers. The ability to take some of our heritage and connect it with someone else's insights and create this new collection is really powerful and exciting. 

What separates Timberland from other likeminded brands? How have you been able to be so successful this long?
I think we're fortunate. There were times in the past 40 years that were hard times, too. I think right now, we're benefited by not just one thing, but a host of things. I think we have to be thoughtful of this time we're given. I think the boot trend is echoed by a macro style trend, whether it be the merging of '90s styles, and this need for authenticity and heritage. Timberland seems to come right into people's radar.

What's good about it is there's are a lot of core consumers who've bought Timberland in the past, but there's another generation now that is new to Timberland that's seeing the same authenticity, the same things that brought other generations to the brand. So this moment, I think, is a really important one for design but also for style.

What can we expect from Timberland now that the brand has hit its 40th anniversary?
If I were to echo our marketing campaign, which we've been using for several seasons now, it's this idea of "Best Then. Better Now." The opportunity is how do you still be modern and recognizable? I think it's really in things that are important, things like material, detail, quality, craftsmanship, also the voice. 

In the future, the "Better Now" is to offer style in surprising ways, where people come in and say, "Wow. I used to wear that from Timberland but I didn't know you made that." It's a real versatile side of Timberland, where you could wear that iconic look but you could wear it for a range of other things, and still not compromise that Timberland identity. It's still stylish. It's gotta look good is the bottom line.

But also the second point of that is it's got to work. If it has the Timberland logo on it it has to mean something. How do we earn the mark of the tree? It's not just pasted on, it's not just stuck on. It's almost that last step in the process where the style looks right, it's modern, it's trend right in the sense that that's a trend Timberland can talk about, and then it performs, and it has a green component. 

Do you guys have any new collaborations planned for the upcoming year? 
We have one that we’re pretty excited about. We have many—I mean, all of them we’re very excited about—but I think we can talk about the Hazel Highway program. We're using iconic leather that was inspired by a boot called the Super Boot which was a really important boot for us. We put this collection together based on that actual leather and trying to capture that look and the feel of that original boot that we saw in the Super Boot. But I think some of the Field Boot, even bringing back the 6-inch field boot, going through our old catalogues and really... It’s almost a bespoke classic in the sense it’s been reinterpreted, but I think for many people they’ll remember, “Oh wow I know where that comes from” because of the iconic nature of that material. 

I mentioned the 10.Deep collection. We have a seasonal kick-off with Black Scale, a first time collab.

What are your thoughts on Timberland's relevancy in hip-hop? How does it feel to have all these rappers and all these kids wanting to wear Timberland's boots?
I think whether it be rappers, musicians, people that are super style conscious about how they put themselves together, this generation's change and also the technology that we have in our hands allows for beautiful ideas that were once regional only to be shared globally and people are able to respond to that. And so the nature of regional style is merging with generational. It's this ability to synthesize an idea from my dad’s generation, my granddad’s generation, and what my kids are thinking about all at the same time. People are mixing and curating their own style, they're navigating time and style at the same time, and they’re making their own decisions.

Timberland is lucky and fortunate that it’s being reconnected, reinterpreted, recruited. It might be some in hip-hop, but it might be some hipsters or it could be a weird mix of many generations all sort of rethinking Timberland in a way like, “Wow I forgot about you but I want to remember you again" and that's a good place to be.