Timberland’s recent foray into fashion has been well-orchestrated. 

The 50-something-year-old workwear boot company has collaborated with the biggest luxury fashion brands, gotten fashion icons to star in its campaigns, and has the most sartorially savvy celebrities in its humble yellow boots.

It’s all culminated in Timberland footwear having a genuine moment. However, Timberland clothing? Not so much, and an enigmatic Japanese design collective is working to change that.

The Tokyo Design Collective, the same group making Vans clothing cool, has been quietly renovating Timberland’s clothing selection. 

A couple of years ago, it launched a concept store and exclusive line called Timberland +81 3 in Tokyo, delivering streetwear-flavored preppy clothing. And its seasonal collections offer much of the same, but with a more rugged, outdoorsy twist. (Timberland is an outdoor clothing brand, after all.)

Look to its newly launched Spring/Summer 2025 collection, and you find a classic long mac jacket in 3-layer water-repellent fabric with a utilitarian network of pockets across the front. Or there is the short-sleeve plaid shirt, adjustable through a drawstring at the bottom so you can cinch it up like you would a waterproof jacket.

From the preppy checkered socks to the military-inspired cagoule, the whole collection toys with themes of Americana, given contemporary twists aimed towards Tokyo’s fashion scene. Which brings me onto the only downside of this collection: It’s an Asia-exclusive collection, available now from Timberland’s Japanese website and stores. 

For those of us outside of Asia, this makes it difficult to get our hands on anything from the drop. Though, thanks to the power of technology, it is not impossible. 

And if Timberland’s recent footwear experiments are anything to go by, there’ll be equally stylish clothing hitting the rest of the world soon.