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

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

More than just your average men's shoe. These shoes mix premium leathers and suedes with athletic and refined styling.  Featuring comfy padded collars and traction-loving outsoles to keep you on the move.

  • Premium nubuck leather uppers
  • Cotton laces
  • Padded collars
  • EVA footbeds
  • 34% recycled rubber siped outsoles are designed for slip resistance
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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.