Research into anti-icing surfaces often conflates the two separate problems of ice accumulation: water adhesion and ice adhesion. The body feathers of perpetually ice-free penguins are very good natural examples of anti-icing surfaces, which use two different mitigation strategies for the two disparate problems. Herein, we mimic the form of the feather’s wire-like structure, which is decorated with superimposed nanogrooves by laser micromachining fine woven wire cloths. Post-processing techniques also allow us to isolate the role of surface chemistry by creating both hydrophilic and hydrophobic versions of the synthetic anti-icing surfaces. Our results show that water-shedding and ice-shedding characteristics are indeed derived from different physical functions of the hierarchical structure. The microstructure of the woven wire cloth leads to facile interfacial cracking and therefore extremely low ice adhesion strengths; the superimposed laser-induced periodic surface structures with hydrophobic surface chemistry lead to water shedding. Our work shows that by first taking a fracture mechanics approach to designing the ice-shedding function, a robust anti-icing surface can be engineered by separately designing the water-shedding functions.