Timberland is making the most of the frigid winter weather, having just released a brand-new special-edition “Road Trip” footwear collection along with reaching into its apparel archive with new outerwear reissues.
The Road Trip collection is highlighted by the Timberland Premium 6-Inch Waterproof Boot ($210) and also includes the brand’s Premium Mid Waterproof Chukka Boot ($160) and Euro Hiker Boot ($120) models. According to Timberland, the series is inspired by the “craftsmanship and fine-stitching of vintage car interiors.”
Each pair in the collection dons matching rust full-grain leather, but it’s the Premium 6-Inch Waterproof Boot that takes the vehicular theme even further with decorative steering wheel-like stitching along the heel and perforated black leather on the shoe’s signature padded collar. Dark gray shoelaces add some contrast to the premium look, with metallic silver hardware and white contrast stitching rounding out the style.
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While not as ornate as some of Timberland’s other limited-edition versions of the iconic 6-inch boot such as a recent patchwork collaboration with Supreme, or the popular woven leather version, the Road Trip style is a subtle way to keep things interesting while maintaining the model’s most distinct features.
As usual, the boot includes 400 grams of PrimaLoft insulation and a dual-density rubber outsole that will ward off any boneless Timb accusations.
In addition to the new footwear, Timberland just re-released two archive jackets; the Granite State Waterproof Rain Jacket ($270), originally released in 2000, and the Welch Mountain Leather Puffer ($1,000) from 1997.
The former is notable for its insulated, waterproof construction and retro color blocking, while the puffer uses a 100-percent nappa sheepskin leather. Both jackets were featured in Timberland’s fall 2025 “Advice of an Icon” campaign, where they were worn by Spike Lee and Skepta.
The Timberland Road Trip collection and new outerwear pieces are available now from timberland.com in limited quantities.
