Footwear having a textured surface. The footwear may have an upper, where at least a portion of the footwear upper has a textured surface. The textured surface may be formed, at least in part, by contoured structures. These contoured structures may define a group of alternating peaks and troughs extending in two orthogonal directions. The textured surface may optionally include apertures that will allow air to pass through the upper into the shoe, and allow moisture to expire from the inside of the shoe into the air.