Good to know

The low-top Timberland Adventure 2.0 Cupsole Alpine Oxford is exclusively available in men's sizes that range from 7 to 13. The kick's leather upper is constructed to fit true to size.

With an abundant cushioning in the collar and tongue areas along with the anti-fatigue footbed, users are treated to a comfortable fit and in-step feel. Although reports of ankle chaffing have been received, the leather upper eventually softens over time. Using Blister Plasters is recommended to assist with the break-in process.

Sport the ultimate in hardwearing elegance with the Timberland Adventure 2.0 Cupsole Oxford. A little bit refined, a little bit street, and a little bit rugged are what defines this shoe. With a classic sneaker silhouette mixed up with rope laces and D-ring metal lace loops, which give it its outdoor-inspired look, and the dapperness of an oxford, this kick could be the perfect choice to bring the wilderness to the city stylishly.

The guys were spotted rocking this pair with jeans to khakis and chinos. Match your jeans with a shirt and stylish outerwear for a dressy yet laidback look or opt for a button-down shirt finished with a coat to exude a grown-up swagger vibe. Ladies can switch it up by interchanging between shorts, dresses, leggings, and shorts.

The first thing you'll notice in this kick is its stylishly unique colorways crafted in premium nubuck leather that gives off a luxurious and elegant look. Another feature that's unique and eye-catching is the materials used in its lace-up system: metal D-ring eyelets and rope laces with reflective accents - this feature provide the kick its rugged aesthetic. Finally, the brand's emblem is embedded on the kick's lateral rear side, which acts as a seal of excellent quality and durability.

Prior to the brand's official launch in 1973, Timberland has been manufacturing the "6-inch yellow cleat" for years. It was the cleat's success that made the brand's commencement and eventual growth possible. They became known for the superb quality and style of the cleat and inevitably reached international status because of it. The following years since the brand's official introduction, their inventory expanded from just the yellow cleats to casual shoes and boat shoes, which also further helped the company's popularity.

Today, Timberland remains pertinent in the footwear game thanks in part to the steady growth of their product range that now includes apparel, watches, backpacks, kids' footwear, and more lifestyle-based shoes. One of the brand's many lifestyle kicks is the Timberland Adventure 2.0 Cupsole Alpine Oxford, a sneaker with a polished look and the brand's rugged style. The shoe is available in a wide array of neutral and vibrant colorways.

  • This kick is also offered in a texturized upper and gum sole iterations.
  • 50% of the shoe's inner lining is made from recycled plastic bottles, while the laces are 100% recycled and the rubber cup soles' 34% is made from recycled rubber.
  • The pair's anti-fatigue EVA footbed is detachable.


How Timberland Adventure 2.0 Cupsole Alpine Oxford ranks compared to all other shoes
Top 35% sneakers
All sneakers
Top 26% Timberland sneakers
All Timberland sneakers
Top 35% low sneakers
All low sneakers


The current trend of Timberland Adventure 2.0 Cupsole Alpine Oxford.
Compare to another shoe:
Danny McLoughlin
Danny McLoughlin

Danny is a sports nut with a particular interest in football and running. He loves to watch sports as much as he loves to play. Danny was lead researcher on RunRepeat and The PFA’s report into Racial Bias in Football Commentary. His football and running research has been featured in The Guardian, BBC, New York Times and Washington Post.