High heel use in professional environments is a common occupational norm for women, particularly in the hospitality, retail, and fashion industries. However, extended and repetitive use may increase the risk of ankle injuries. The objective of this exploratory cross-sectional study was to examine the factors associated with a history of ankle sprain among women wearing high heels at work. A total of 203 participants were recruited from selected workplaces in Lahore, Pakistan, via a nonprobability convenience sampling technique. Data were collected through a structured questionnaire assessing sociodemographic information, footwear usage patterns, pain symptoms, occupational standing duration, and ankle sprain history. Chi-square analysis revealed significant associations between ankle sprains and heel height, duration of heel wear, type of heel, workplace footwear requirements, and the presence of pain during high heel use (p < 0.05). Women wearing heels ≥10 cm and those wearing stilettos were more likely to report a history of ankle sprain. Logistic regression analysis revealed that standing more than 4 hours per day (OR = 3.803), footwear requirements at work (OR = 3.534), and pain during heel use (OR = 9.893) significantly increased the odds of experiencing an ankle sprain, whereas increasing age (OR = 0.789) and being married (OR = 0.304) were associated with lower risk (p < 0.05). Ankle sprains led to productivity loss in more than 75% of the participants, with the majority missing 1–5 workdays. These findings highlight the occupational health risks linked to high heel use and suggest that prolonged standing, footwear mandates, and early pain symptoms are important predictors of injury. Preventive workplace strategies—such as ergonomic footwear policies, standing breaks, and employee education—are essential for reducing ankle injury risk among women in high heel–requiring professions.