Obesity as a multi-organ disease that affects the entire human organism. Notably, the skin is no exclusion from this postulate. Skin changes in obese patients have been widely studied with regards to mechanical friction, skin infections, and skin hypertrophic conditions, such as acanthosis nigricans and, most commonly, fibromas (skin tags). Almost 60–70% of obese patients present with a variety of skin changes. Herein, we discuss our own experience and review the complex skin changes in obesity. The role of metabolic syndrome and obesity are responsible for the epidemiological prevalence and are involved in the pathogenesis of chronic inflammatory skin diseases, such as psoriasis, atopic dermatitis, and skin malignancies. Here, we comment on the role of nutritional interventions in these patients as it has been proven that low-calorie diet and weight loss is related to improvement of inflammatory skin diseases. The readership of this paper will receive up-to-date overview on the connection between obesity and the skin that is of a practical importance to any clinician working in the field.