The skin is the largest organ in the body and one of the primary barriers to the environment. In order to optimally protect the host, the skin is home to numerous immune cell subsets that interact with each other and other non-immune cells to maintain organ integrity and function. Regulatory T cells (Tregs) are one of the largest immune cell subsets in skin. They play a critical role in regulating inflammation and facilitating organ repair. In doing so, they adopt unique and specialized tissue-specific functions. In this review, we compare and contrast the role of Tregs in cutaneous immune disorders from mice and humans, with a specific focus on scleroderma, alopecia areata, atopic dermatitis, cutaneous lupus erythematosus and psoriasis.