Ordered arrays of nanopillars with controlled tip shapes were fabricated by a template formation process using anodic porous alumina with controlled pore shapes. Although various studies have been reported on the preparation of nanopillar arrays using anodic porous alumina as a template, there have been no reports on the formation of nanopillar arrays with precisely controlled tip shapes. Re-anodization of anodized samples in a neutral electrolyte can flatten the bottom of pores. The use of the resulting anodic porous alumina as a template enabled the fabrication of ordered nanopillar arrays with a flattened tip. The formation of overhanging nanopillar arrays was also possible by using anodic porous alumina with a controlled pore shape as a template, which was fabricated by a combination of anodization, TiO2 coating by atomic layer deposition, and pore-widening treatment. The contact angles of water and oil droplets were measured using the obtained polymer nanopillar arrays with controlled tip shapes. The contact angle of water droplets did not change regardless of the tip shape of the nanopillars, whereas the contact angle of oil droplets changed depending on the tip shape of the nanopillars. This indicates that liquids with high surface tension are not affected by the nanopillar tip shape, whereas liquids with low surface tension are greatly affected by the nanopillar tip shape. Among the nanopillar arrays fabricated in this study, it was confirmed that the overhanging nanopillar array with many edge structures that have the pinning effect of suppressing the wetting spread of the solution exhibited the highest oil repellency. The method reported here can be used to fabricate nanopillar arrays with a precisely controlled tip geometry, and it is expected that optimization of the geometry will further improve the water- and oil-repellent properties.