In the dynamic world of fashion, high-heeled footwear is revered as a symbol of style, luxury and sophistication. Yet, beneath the facade of elegance of classy footwear lies the harsh reality of discomfort and pain. Thus, this study aims to investigate the influence of wearing high-heeled shoes on the sensation of pain across different body regions over a period of 6 h. It involved fifty female participants, all habitual wearers of high-heeled shoes, aged between 20 and 30 years. Each participant kept a record of their perceptions of pain and discomfort every hour for a total of 6 h using a 0–10 pain scale with 0 indicating no pain and 10 indicating severe pain. The findings reveal a progressive rise in pain throughout wear, with the most intense pain reported in the back, calcaneus, and metatarsals. The analysis shows that after approximately 3.5 h, participants experience significant increases in pain levels. However, the relationship between heel height and pain is not linear. It appears that a heel height of 7.5 cm is the threshold where overall body pain becomes significant. The study suggests that a duration of 3.5 h of wear and a heel height of 7.5 cm serve as critical points to decrease overall body pain. Moreover, beyond this heel height, knee pain diminishes compared to other body areas possibly due to the shift towards a more neutral posture. The study findings, coupled with the recommendations, can assist footwear designers in crafting not only stylish but also comfortable shoes.