We spent 7.4 hours reading reviews from experts and users. In summary, this is what sneaker fanatics think:

6 reasons to buy

  • According to several commenters, the Timberland Adventure 2.0 Cupsole Alpine Chukka is comfortable right out of the box.  
  • Most reviewers agree that the sneaker looks very stylish.
  • Several users have observed that the shoe is made of good quality materials.
  • A few testers have revealed that the Timberland Adventure 2.0 Cupsole Alpine Chukka is a lightweight model.
  • More than a handful of buyers impart that they will recommend the sneaker to someone else. 
  • This model comes in several color options.

2 reasons not to buy

  • This Timberland Adventure 2.0 Cupsole Alpine Chukka stains easily, a couple of wearers have complained.  
  • A few reviewers find the Timberland Adventure 2.0 Cupsole Alpine Chukka’s features disappointing compared to other Timberland lifestyle shoes.

Bottom line

Timberland is known for its outdoor cleats, and that heritage has inspired the Adventure 2.0 Cupsole Alpine Chukka. As a casual sneaker, this model takes inspiration from the classic design of the chukka, updating it for modern style. 

Comfortable, lightweight, and stylish, this shoe is a good option for adventurers looking for laidback footwear. Despite this, users have also found some issues with the model. It’s said to stain very easily and pales in comparison to the brand’s other kicks.


Top: Mid
Inspired from: Casual
Collection: Timberland Casual Shoes
Closure: Laces
Material: Nubuck, Rubber Sole
Price: $130
Colorways: Black
Small True to size Large
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A top rated sneaker
A top rated Timberland sneaker
A popular pick
It has never been more popular than this February

A durable fit is ensured by the premium leather upper of the Timberland Adventure 2.0 Cupsole Alpine Chukka. For this model, men’s sizes are offered. Laces and D-ring eyelets maintain a snug fit. Lastly, the mid-cut collar provides excellent protection for the ankle.

Trademark Timberland details elevate this shoe to a level of sophistication that makes it appropriate for any casual activity. Whether it's for the streets or the office, these kicks are worth a place in anyone's wardrobe. Urban outings or weekend getaways also become more stylish with a pair of these sneakers. Pants or shorts paired with t-shirts and jackets complete these shoes’ flair for urban adventure. 

An upper made up of premium nubuck leather that comes in several colors lends a classic appeal to the Timberland Adventure 2.0 Cupsole Alpine Chukka. Its collar is padded for more comfort, while its mesh lining ensures ventilation. The Timberland Tree logo is debossed on the side, while the brand name is found on the tongue and heel tab.

Founder Nathan Swartz began working in the footwear industry in the late 1920s. In 1955, he bought all the shares in the Boston-based The Abington Shoe Company, bringing his sons with him to the business. Contract work for manufacturers was their main operation back then, but it all changed when they introduced the injection-molding process in the shoe industry. The technology allowed the company to remove the need for stitching the sole to the upper.

Soon, the business turned to the production of completely waterproof cleats for both cold and warm weather. By the late 1960s, the company had grown so much that they transferred to Newmarket, New Hampshire. It was here that they came up with a waterproof leather cleat called “Timberland” in 1973. It quickly became so popular that the brand decided to change its name to The Timberland Company.

It was also in the 1970s that boat shoes and casual footwear were added to the brand’s cleat lineup. One shoe from the company’s casual series is the high-top Timberland Adventure 2.0 Cupsole Alpine Chukka. It's inspired by the brand's distinct outdoor roots, as can be seen in its smooth upper, made up of premium leather. Its design has a touch of elegance, yet it also has a rugged appeal that speaks of adventure. 

  • The EVA footbed offers support and comfort.
  • Comfort is also delivered by the cupsole.
  • Its rubber outsole has a siped design that makes it excellent for slip resistance.
  • This model was also crafted with some eco-conscious materials to reflect the brand’s commitment to the natural world.


Danny McLoughlin

Danny is a sneakerhead turned sneaker industry expert that believes a good outfit begins from the feet up. His aunt currently isn't speaking to him for wearing a pair of kicks at his cousin's wedding. He spends most of his time trying to keep on top of the latest releases, hitting up his contacts and doing what needs to be done to secure his next pickup. Danny has been featured in prestigious publications such as The Washington Post, The Irish Times, Footwear News and the like.