Verdict from 100+ user reviews

10 reasons to buy

  • The Timberland Adventure Cupsole Chukka is an affordable sneaker.
  • Many testers love the look of the shoe, calling it attractive and sporty.
  • It fits true to size, most reviewers confirm.
  • A couple of wearers observe that the Timberland Adventure Cupsole Chukka keeps their feet dry.
  • The sneaker fits very comfortably, a lot of commenters attest.
  • Most buyers say that they can recommend the shoe to others.
  • A few users like the Timberland Adventure Cupsole Chukka so much that they have multiple pairs.
  • There are several colorways released for the model.
  • The kicks offer a high level of quality that a lot of reviewers have come to expect of Timberland sneakers.
  • Some testers share that they get compliments every time they wear the Timberland Adventure Cupsole Chukka.

1 reason not to buy

  • A few testers remark that the model needs to broken in first as the fit is initially tight.

Bottom line

Combining the timeless design of a cleat with the function and comfort of a sneaker, the Timberland Adventure Cupsole Chukka readies the wearer for any journey. It offers value for the money at $120, providing support and durability.

Reviewers have pointed out that the sneaker is attractive and fits true to size. They receive compliments from others due to the shoe’s head-turning style. However, a few buyers have remarked that it has to be broken in first due to its initial tight fit.

Tip: see the best sneakers.

Good to know

The Timberland Adventure Cupsole Chukka is in men’s sizes 7-13, offered in medium width. Its upper could be made up of suede, nubuck, or full-grain leather material, depending on the chosen colorway. This model has a mid-top collar that provides ankle protection, while the lace-up front secures the fit.

Several colorways are available for the mid-top Timberland Adventure Cupsole Chukka cleat. The selections are burnished wheat nubuck, olive full-grain, medium brown full-grain, and black nubuck. With its chukka cleat design, the kick delivers an outdoor-inspired look that’s ideal for various casual ensembles.

The sneakers will look particularly stylish with a pair of pants or jeans, which will emphasize its high-cut construction. A simple t-shirt in neutral shades or a sweatshirt can complete the casual yet elegant flair. Shorts or jogger pants will also go well with the shoes, resulting in a laidback flair.

The Timberland Adventure Cupsole Chukka by the Timberland brand elevates a mid-top silhouette to casual sophistication. Its upper is built with premium suede, nubuck material, or full-grain leather, providing a smooth appeal. It’s complemented by the laces, which are either fully organic cotton or authentic rawhide.

This shoe has eco-friendly features that aim to lessen impact against the environment. The footbed covers are constructed entirely from recycled plastic bottles. Meanwhile, the rubber siped outsole, which is designed for slip resistance, is made up of 34% recycled rubber.

Timberland was founded in 1928 by the American shoemaker Nathan Swartz. The company started in Boston, Massachusetts, and now has its headquarters in New Hampshire. Today, the brand is known for its high-quality outdoor gear, apparel, and most notably, footwear.

With the name Timberland, hiking and other outdoor shoes come to mind. However, the brand is also slowly becoming recognized for its lifestyle sneakers, which often combine outdoor inspirations and features with casual designs. Such a blend has resulted in such models as the Timberland Adventure Cupsole Chukka shoes.

This sneaker is dubbed as not the average men's footwear. In the signature Timberland style, it is crafted from a premium mix of materials, consisting of leather and suede. It has a refined style combined with athletic touches, making it ideal for a streamlined, casual style.

  • The collar is padded to offer extra comfort around the ankle.
  • Extra soft linings provide an ultra-comfortable and breathable feel.


How Timberland Adventure Cupsole Chukka ranks compared to all other shoes
Top 47% sneakers
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Bottom 45% Timberland sneakers
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Top 42% mid sneakers
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The current trend of Timberland Adventure Cupsole Chukka.
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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.