Surfactants possess the ability to reduce surface tension at low concentrations, resulting in emulsification, foaming, wetting, and solubilizing. As a versatile industrial material, surfactants can be widely used as additives in the industrial field as different as textile, metal processing, mineral processing, new materials, industrial cleaning, construction, and pharmaceuticals. The most extensive application of surfactants perhaps is in the household and cosmetic industries, such as laundry detergents, dishwashing detergents, facial and body cleansers, and preparation of emulsions and creams. However, the extensive use of detergents, cleaners, and cleansers on skin may cause itching, redness, and dryness termed as surfactant-induced irritation, which is at least, partially due to surfactant penetration into skin. To understand how surfactants penetrate into skin, this review summarizes the penetration models proposed by researchers in the past two decades, including the surfactant monomer penetration model, the surfactant micelle and submicelle penetration model, and the recently proposed surfactant charge density and penetration correlation model that demonstrates the correlation between the surfactant charge density and skin penetration.