Background: Treatments for oral squamous cell carcinomas (OSCCs) often result in significant aesthetic and functional issues, impacting patients’ quality of life (QoL). The COVID-19 pandemic’s mask mandates may have provided psychosocial benefits by concealing facial disfigurements, potentially reducing stigma. This study aimed to assess the impact of mask-wearing on the QoL of patients surgically treated for OSCC. Methods: This single-center, cross-sectional study, conducted from June 2022 to December 2023, included patients who had completed their treatment and returned home before or during the mask-wearing mandate. They answered a questionnaire using a four-point Likert scale to evaluate the mask-wearing’s impact on QoL and the influence on it of physical appearance, tumor localization, radiotherapy, and treatment end date. Results: The questionnaire analysis found a high internal consistency among the questions (Cronbach’s alpha = 0.931). Considering 41 patients (median age 69, 63% male), wearing a mask significantly improved QoL, with a mean score of 1.66 compared to a score of 2.00 for patients not wearing it (p < 0.001). This improvement was particularly notable for appearance concerns, fear of perception by family or others, and sociability apprehension. The QoL, with or without mask use, was not significantly modified when considering physical appearance, tumor localization, radiotherapy, or end date of the treatment, as demonstrated by two-way ANOVA tests and multiple linear regression. Conclusions: Mask-wearing positively impacted QoL in OSCC patients, providing psychological relief from disfigurement and social stigma. Masks offer a simple, accessible solution to enhance QoL while awaiting a definitive prosthetic treatment, suggesting that their continued use could be beneficial in supportive care strategies.