Flexible wearable pressure sensors have drawn tremendous interest for various applications in wearable healthcare monitoring, disease diagnostics, and human–machine interaction. However, the limited sensing range (<10%), low sensing sensitivity at small strains, limited mechanical stability at high strains, and complicated fabrication process restrict the extensive applications of these sensors for ultrasensitive full‐range healthcare monitoring. Herein, a flexible wearable pressure sensor is presented with a hierarchically microstructured framework combining microcrack and interlocking, bioinspired by the crack‐shaped mechanosensory systems of spiders and the wing‐locking sensing systems of beetles. The sensor exhibits wide full‐range healthcare monitoring under strain deformations of 0.2–80%, fast response/recovery time (22 ms/20 ms), high sensitivity, the ultrasensitive loading sensing of a feather (25 mg), the potential to predict the health of patients with early‐stage Parkinson's disease with the imitated static tremor, and excellent reproducibility over 10 000 cycles. Meanwhile, the sensor can be assembled as smart artificial electronic skins (E‐skins) for simultaneously mapping the pressure distribution and shape of touching sensing. Furthermore, it can be attached onto the legs of a smart robot and coupled to a wireless transmitter for wirelessly monitoring human‐motion interactivities.