Icing causes many problems in daily life and with equipment stability, and many efforts have been made to remove surface icing. Herein, a novel organic gel-infused porous material is developed to achieve excellent de-icing performance. Porous polydimethylsiloxane (P-PDMS) composites with different pore sizes were prepared by a template method. The two-phase skeletons and/or gel material was obtained by infusing PDMS gel into P-PDMS (GIP-PDMS). The ice adhesion strength of GIP-PDMS under static and dynamic icing conditions was comparatively investigated. The results show that GIP-PDMS displayed excellent anti-icing performance, and the delay freezing time of GIP-PDMS1 was ∼4554 s at −5 °C. The ice adhesion strength of GIP-PDMS was much lower than that of P-PDMS, owing to the distinct modulus between the two-phase skeletons and/or gel. The simulation results indicated that the stress concentration promoted ice fracture and contributed to weak ice adhesion. Molecular dynamics further showed that the state of the molecular chains and the interfacial interaction between ice and PDMS gel at 268 K helped to decrease the shear force.