The surface quality of chamfer milling of stainless steel is closed related to the products of 3C (Computer, Communication and Consumer electronics), where a cutter is a major part to achieve that. Targeting a high-quality cutter, an experimental evaluation is carried out on the influence of grinding texture of cutter flank face on surface quality. The mathematic models of chamfer cutter are established, and they are validated by a numerical simulation. Also the grinding data are generated by the models and tested by a grinding simulation for safety reasons. Then, a set of chamfer cutting tools are machined in a five-axis CNC grinding machine, and consist of five angles between the cutting edge and the grinding texture on the 1st flank faces, i.e., 0°, 15°, 30°, 45° and 60°. Furthermore, the machined cutting tools are tested in a series of milling experiments of chamfer hole of stainless steel, where cutting forces and surface morphologies are measured and observed. The results show that the best state of both surface quality and cutting force is archived by the tool with 45° grinding texture, which can provide a support for manufacturing of cutting tool used in chamfer milling.