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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.


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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.