We herein introduce a lightweight and zero-power smart face mask, capable of wirelessly monitoring coughs in real time and identifying proper mask wearing in public places during a pandemic. The smart face mask relies on the compact, battery-free radio frequency (RF) harmonic transponder, which is attached to the inner layer of the mask for detecting its separation from the face. Specifically, the RF transponder composed of miniature antennas and passive frequency multiplier is made of spray-printed silver nanowires (AgNWs) coated with a poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) passivation layer and the recently discovered multiscale porous polystyrene-<i>block</i>-poly(ethylene-<i>ran</i>-butylene)-<i>block</i>-polystyrene (SEBS) substrate. Unlike conventional on-chip or on-board wireless sensors, the SEBS-AgNWs/PEDOT:PSS-based RF transponder is lightweight, stretchable, breathable, and comfortable. In addition, this wireless device has excellent resilience and robustness in long-term and repeated usages (i.e., repeated placement and removal of the soft transponder on the mask). We foresee that this wireless smart face mask, providing simultaneous cough and mask-wearing monitoring, may mitigate virus-transmissive events by tracking the potential contagious person and identifying mask-wearing conditions. Moreover, the ability to wirelessly assess cough frequencies may improve diagnosis accuracy for dealing with several diseases, such as chronic obstructive pulmonary disease.