A digital makeup artist system includes a mobile device, a database system storing cosmetic routine information, common makeup looks, cosmetic products for skin types and ethnicity, and user look preferences of a user. The mobile device includes a user interface for interacting with a digital makeup artist. The digital makeup artist performs an interactive dialog with the user in order to capture needs of the user, including types of makeup look, indoor or outdoor look, skin condition, facial problem areas, favorite facial features. The computation circuitry analyzes the user's face image to identify face parts, analyzes the face image to determine facial characteristics, and generates image frames to be displayed in synchronization with the interaction with the digital makeup artist based on the analyzed face image, needs of the user, the stored cosmetic routine information, common makeup looks, cosmetic products for skin types and ethnicity, and the user look preferences.