Lipstick has been a dominant beauty practice across cultures and throughout history. Once deemed a sign of Satan, a potential health risk, and even an illegal product, lipstick has experienced centuries of controversy to secure its status as a marketplace icon - albeit a polarising one. Liberating to some; limiting to others. How have such tensions shaped lipstick's cultural meanings? By examining lipstick's gendered history, we highlight how lipstick reflects contested feminist politics of choice - regarded as playful and deliberately chosen as well as fostering appearance-based expectations based on idealised feminine beauty. We highlight how lipstick gives rise to tensions between empowerment and oppression across three main themes: self-expression and choice, privilege and choice, and morality and choice. We conclude that for lipstick to be pleasurable and freely chosen, it must first be decoupled from patriarchal standards of ideal feminine beauty for women.