Ever since the emergence of the ongoing COVID-19 pandemic, the usage of makeshift facemasks is generally advised by policymakers as a possible substitute for commercially available surgical or N95 face masks. Although such endorsements could be economical and easily accessible in various low per-capita countries, the experimental evidence on the effectiveness of such recommendations is still lacking. In this regard, we carried out a detailed experimental investigation to study the fate of a large-sized surrogate cough droplet impingement at different velocities (corresponding to mild to severe coughs) on various locally procured cloth fabrics. Observation shows that larger ejected droplets (droplets that would normally settle as fomites in general) during a coughing event have enough momentum to penetrate single-layer cloth masks; the penetrated volume atomize into smaller daughter droplets that fall within aerosol range, thereby increasing infection potential. Theoretically, two essential criteria based on the balances of viscous dissipation-kinetic energy and surface tension-kinetic energy effects have been suggested for the droplet penetration through mask layers. Furthermore, a new parameter called η (the number density of pores for a fabric) is developed to characterize the volume penetration potential and subsequent daughter droplet size. Finally, the effect of mask washing frequency is analyzed. The outcomes from the current study can be used as a guide in selecting cloth fabrics for stitching multi-layered.