Abstract Introduction: Mask-related dermatoses have been widely reported in adults since the global COVID-19 pandemic. Compulsory mask wearing has been mandated in many countries. As pediatric dermatologists, we aim to characterize different types of mask-related dermatoses in the pediatric population, evaluate the prevalence, and potential exacerbating and mitigating factors to improve compliance in children in this era of regular mask wearing. Methods: We conducted a cross-sectional study from November 1, 2020, to January 31, 2021, at a tertiary hospital in the form of an anonymous online questionnaire. This included all children aged (2–20 years old) in our pediatric dermatology clinics, tertiary education students (16–20 years old), and children of hospital/health-care cluster staff (2–20 years old). Results: Of the 577 participants who reported regular mask wearing, 140 (24.3%) reported symptoms. The most common symptoms were itching (74.5%), dryness (49.6%), dyspnea (32.1%), and oily skin (29.9%). The most common rashes were acne (48.9%), eczema (27%), dryness/peeling (23.4%), urticaria (18.2%), and cheilitis (16.8%). The most statistically significant risk factors for developing mask-related symptoms and/or rashes were (a) prolonged duration of mask wearing/day and (b) preexisting dermatoses and/or atopic history (especially atopic dermatitis). Conclusions: As the pediatric population remains vulnerable to emerging COVID-19 variants and other respiratory viruses, masks remain an important form of protection in daily life. Like in adults, regular mask wearing can lead to various facial symptoms/dermatoses in pediatric wearers, adding to dermatological burden during a pandemic. Those with preexisting risk factors should be made aware of this. We recommend all pediatric mask wearers should not exceed continuous mask wearing for 4 h and to take scheduled “mask breaks” in safe, well-ventilated areas.