Homelessness in the United States is a significant public health issue, with dermatologic disease being the most prevalent health concern among the undomiciled and sheltered populations. Despite a growing need for dermatologic care, the supply of dermatologists remains insufficient, contributing to disparities in healthcare access for this vulnerable group. This review aims to detail the spectrum of dermatologic conditions experienced by homeless individuals, identify barriers to adequate care, and explore teledermatology as a potential solution to bridge these gaps. A comprehensive literature review was conducted, analyzing studies and reports on dermatologic issues prevalent among the homeless population and the efficacy of teledermatology in addressing these concerns. Homeless individuals face a wide range of dermatologic problems, from common conditions like acne and eczema to severe issues such as cellulitis, leg ulcers, and skin cancer. Drug abuse, domestic and sexual abuse, and parasitic infestations further complicate the dermatologic health of this population. Teledermatology has emerged as a promising tool to enhance access to dermatologic care, showing significant improvements in clinical outcomes and accessibility, especially in underserved urban settings. However, challenges remain, such as the digital divide affecting the elderly and low-income populations, which could potentially exacerbate disparities. Addressing the dermatologic needs of the homeless population requires a multifaceted approach. Teledermatology offers a viable solution to improve care access and efficiency, but additional efforts are necessary to ensure inclusivity and avoid further marginalization. Volunteer-driven multidisciplinary clinics also play a crucial role in providing care, though they face challenges in continuity and resource availability. Future strategies should focus on integrating teledermatology with other supportive services to create a comprehensive care model for this underserved population.