The little black dress (LBD) has evolved from a minimalist garment introduced by Chanel into a powerful cultural symbol that reflects the transformation of female consciousness throughout modern history. This paper investigates the semantic, cultural, and ideological meanings embedded in the LBD across different periods, focusing on how its changing design aesthetics mirror shifting perceptions of femininity, empowerment, and social identity. By analyzing visual materials, fashion designs, artworks, and advertisements from the Victorian era to contemporary popular culture, the study demonstrates that the LBD has been repeatedly reinterpreted as a site where gender norms are challenged, reconstructed, or reclaimed. The evolution of the LBD—from mourning attire to modernist neutrality, to a signifier of elegance, and finally to a medium of personal agency—reveals broader societal transformations regarding women’s autonomy and self-expression. Ultimately, the LBD functions not only as a fashion item but also as a semiotic vehicle documenting the progress of women’s roles and rights in society.