COVID-19 has forced humankind to adopt face masks as an integral part of everyday life. This preventive measure is an effective source control technique to curb the spread of COVID-19 and other similar diseases. The virus responsible for causing COVID-19 has undergone several mutations in the recent past, including B.1.1.7, B.1.351, P.1, and N501Y, B.1.617, with a higher infectious rate. These viruses' variants are mainly responsible for the recent spike in COVID-19 cases and associated steep rise in mortality rate worldwide. Under these circumstances, the Center for Disease Control (CDC) and health experts recommend double masking, which mainly includes a surgical mask and a cotton mask for the general public. This combination provides an additional layer of protection and masks fitment to minimize the leakage of droplets expelled during coughing, sneezing, talking, and breathing. This leakage may cause airborne transmission of the virus. In the present study, we report a systematic quantitative unsteady pressure measurement supplement with flow visualization to quantify the effectiveness of a single and double mask. We have also evaluated double masking consisting of a surgical mask and an N-95 mask used by medical professionals. A simple knot improves the surgical mask fitment significantly, and hence, the leakage of droplets is minimized. The leakage of the droplets was reduced to a large extent by using a double mask combination of a two-layer cotton mask over the surgical mask with a knot. The double mask combination of surgical + N-95 and two-layer cotton + N-95 masks showed the most promising results, and no leakage of the droplets is observed in the forward direction. A double mask combination of surgical and N-95 mask offers 8.6% and 5.6% lower mean and peak pressures compared to surgical, and cotton mask. The best results are observed with cotton and N-95 masks with 54.6% and 23% lower mean and peak pressures than surgical and cotton masks; hence, this combination will offer more comfort to the wearer.