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We're sorry, but the Men's Adventure 2.0 Cupsole Chukka has been discontinued

Don’t worry though, we’ve got some similar products we think you will like

Never stay still with our iconic Cupsole 2.0 silhouettes that counteract the concrete of the urban jungle.
Explore all day and feel good on your feet thanks to a shock-absorbing and supportive EVA footbed.

  • Upper crafted in premium nubuck leather from a Leather Working Group Silver-rated tannery
  • The padded collar cushions a snug ankle
  • Featuring eye-catching square cotton laces in the same colour as the upper
  • Feet stay comfy with soft, breathable PET mesh lining made using 50% recycled plastic bottles
  • The rubber outsole gives top traction and eco-conscious cool with 34% recycled rubber

Style: A1IYD
Colour: Beige

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50% Recycled PET
Decrease your environmental footprint with Timberland® footwear made with recycled PET. One or more major components contain at least 50% recycled polyethylene therephthalate (PET), the plastic used to make soda bottles.
Ortholite Insoles
Stay comfortable all day long with Timberland® footwear featuring lightweight OrthoLite® foam insoles. The ultra-breathable material never loses its ability to absorb shock and also provides moisture management protection and has antimicrobial treatment for odor control.
Recycled Rubber
Combine what you stand for with what you stand on with these 34% Recycled Rubber soles. They deliver the traction and durability you demand whether venturing into nature or commuting to work.
Silver Rated Tannery
Get instant comfort, and karma, with footwear and apparel made with Timberland® leather from tanneries that merit silver ratings from the Leather Working Group for their water, energy and waste management practices. Durable, rugged and beautiful, it will last season after season.