The preparation of the photo-polymerized stain resistant acrylic coating is studied using Fourier transformed infrared spectroscopy, contact angle measurement, gel permeation chromatography, and scanning electron microscopy. The addition of 2,2,2- trifluoroethyl methacrylate (TFEMA) can effectively increase the water contact angle of the acrylic coating from 79.9° (? =1.7°) to 112.1° (? =3.6°) but few differences of hydrophobic behaviors are found in the coatings containing TFEMA more that 20 wt.%. The effect of surface roughness, prepared by changing solvent evaporation rates, adding silica with different particle sizes, and micro-imprinting, on the hydrophobic property of the acrylic coating is also studied. The evaporation rate can affect the contact angle of the acrylic films by changing the porosity of the surface. The addition of a proper size and amount of silicas would significantly increase the surface roughness and then increase the water contact angle to 125.7° (? =3.6°). The template of micro-imprinting with different surface structures is prepared by etching silicone wafers at various conditions. The water contact angle of the wafer can drastically increase from 34.8° (? =3.7°) to 82.0° (? =3.0°) after the etching. A fine replica of the etched wafer surface can be obtained on the surface of the acrylic coatings.