Studying the impact of high-heeled shoes on kinetic changes and perceived discomfort provides a basis to advance the design and minimize the adverse effects on the human musculoskeletal system. Previous studies demonstrated the effects of inserts on kinetics and perceived comfort in flat or running shoes. No study attempted to investigate the effectiveness of inserts in high heel shoes. The purpose of this study was to determine whether increasing heel height and the use of shoe inserts change foot pressure distribution, impact force, and perceived comfort during walking. Ten healthy females volunteered for the study. The heel heights were 1.0cm (flat), 5.1cm (low), and 7.6cm (high). The heel height effects were examined across five shoe-insert conditions of shoe only; heel cup, arch support, metatarsal pad, and total contact insert (TCI). The results indicated that increasing heel height increases impact force (p<0.01), medial forefoot pressure (p<0.01), and perceived discomfort (p<0.01) during walking. A heel cup insert for high-heeled shoes effectively reduced the heel pressure and impact force (p<0.01), an arch support insert reduced the medial forefoot pressure, and both improved footwear comfort (p<0.01). In particular, a TCI reduced heel pressure by 25% and medial forefoot pressure by 24%, attenuate the impact force by 33.2%, and offered higher perceived comfort when compared to the non-insert condition.