This invention is directed to a microstructured filament that can be used to make fibers having an extruded filament having pre-cooled microfeatures in a radial spiral arrangement about a bore though the filament wherein the microfeature has a width in the range of 25 μm to 40 μm and height in the range of 90 μm to 100 μm; and, the filament having a post-cooled state having post-cooled microfeatures having physical dimensions smaller than that of the pre-cooled microfeatures. The filament can include microfeatures having a width in the range of 400 nm to 4 μm and height in the range of 400 nm to 4 μm. The filament and fiber can include physical characteristics selected from the group consisting of: hydrophobicity, self-cleaning, increased hydro-dynamic drag coefficients, decreased or increased aerodynamic drag coefficients, increased friction, reduced friction, optical effects, increased adhesion, decreased adhesion, oleophobicity, tactile effects, anti-blocking and any combination of these.