Bioinspired surface material with re-entrant texture has been proven effective in exhibiting good pressure resistance to droplets with low surface tension under static conditions. In this work, we combined femtosecond laser cutting with shape memory polymer (SMP) and tape to fabricate re-entrant micropillar arrays by proposing a top-restricted self-growth (TRSG) strategy. Our proposed TRSG strategy simplifies the fabrication process and improves the processing efficiency of the re-entrant structure-based surface material. The structural parameters of the re-entrant micropillar array (microdisk diameter D, center-to-center distance P, and height H) can be adjusted through our TRSG processing method. To better characterize the anti-infiltration ability of various re-entrant micropillars, we studied the dynamic process of ethylene glycol droplet deformation by applying external vertical vibration to the surface material. Three parameters (vibration mode, amplitude, and frequency) of the external excitation and structural parameters of the re-entrant micropillar array were systemically investigated. We found that the surface material had better dynamic pressure resistance when P and D of the re-entrant texture were 650 and 500 μm, respectively, after heating for 6 min. This work provides new insights into the preparation and characterization of the surface material, which may find potential applications in microdroplet manipulation, drug testing, and biological sensors.