This paper interrogates the identities in the representations of women adorned in African cultural dress forms in contemporary Nigerian paintings. While many studies have explored the subject of African dress forms from other viewpoints, not many are known to investigate the topic from the perspective of contemporary Nigerian paintings. It is for this reason I purposively selected five paintings from different artists in which they represented women adorned in African dress forms to communicate the expressions of personal, social, religious, and cultural identities within different contexts. Although the contemporary paintings give clues to the expressions of identities in dress, the ideas and meanings conveyed were also interrogated in each work. In engaging the paintings in close case study interrogations, the paper combines formal analysis and cultural history methodologies. Formal analysis is adopted for the analysis of the formal elements in each painting, whereas cultural history is used to contextualise each painting within the culture and history that is recalled to give the representation its proper identity. Besides, the close case study analysis reveals that the artists drew inspiration from the personal aesthetics of women adorned in African dress forms in different Nigerian cultures. Through the representations, three notable African cultural identities are manifested, which include Yoruba, Gwari, or Gbagyi and Hausa cultures, aside from other identities interrogated in each painting.