Footwear assemblies that include a sole assembly and an upper portion secured to the sole assembly. The upper portion includes a tightening structure that extends up a portion of the height of the footwear assembly, and an extension of snakebite material positioned above the tightening arrangement. The extension of snakebite material is typically loose fit around the user's lower leg. The tightening arrangement provides adjustable tightening of the footwear assembly about the user's foot and lower leg at locations below the extension of snakebite material. The footwear assembly can include snakebite resistant material that covers substantially all of the surface area of the upper portion. Additional support, waterproofing, insulating and padding layers or materials can be used throughout the footwear assembly.
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