The COVID-19 pandemic has enveloped the world and there has been a high incidence of occupational dermatoses related to Personal Protective Equipment (PPE) amongst healthcare workers (HCWs) during this period. Prevention and management of these conditions will not only improve staff morale and quality of life, but will also minimize the risk of breaching PPE protocol due to such symptoms. The tropical climate in Singapore predisposes HCWs to more skin damage and pruritus due to intense heat, high humidity and sun exposure. The effects of friction, occlusion, hyperhidrosis and overheating on the skin in the tropics should not be neglected. Preventive measures can be taken based on our recommendations, and the working environment can be made more conducive for frontline HCWs. We review the literature and discuss various preventive and management strategies for these occupational skin diseases for our frontline HCWs, especially those working in less controlled working environments beyond the hospital in Singapore. Shorter shifts and frequent breaks from PPE are recommended. Duration of continuous PPE-usage should not exceed 6 h, with breaks in non-contaminated areas every 2-3 h to hydrate and mitigate the risk of skin reactions. Other strategies, such as teledermatology, should be considered so that consultations can remain accessible, while ensuring the safety and well-being of our clinical staff.