Aim: Comfort is important if good compliance is to be achieved in persons wearing safety shoes. Comfort is mainly determined by the cushioning in the shoes. Optimized cushioning in safety shoes can be demonstrated in short-term tests. It remains uncertain, however, how beneficial improved cushioning is in the long-term and how it is rated by the wearer. The aim of this study was therefore to assess plantar pressure distribution in differently constructed safety shoes during a period of six months. Furthermore, the subjective comfort rating by the wearers of the shoes was recorded during this observation period. Method: A total of 48 workers were randomly assigned either to a prototype shoe group P (improved cushioning) or a standard shoe group S (standard cushioning). All subjects wore the assigned footwear for the subsequent six months during whole work shifts. Plantar pressure distribution (peak pressure [N/cm²]) was measured during walking (3.5 km · h—1 ± 10 %) at the beginning, after three and after six months. In addition a questionnaire rating subjective comfort of the shoes was filled in. Results: Peak pressure on the ball as well as the heel of the foot was significantly less in P than in S throughout the observation period of six months (p = 0.00, peak pressure reduction ~ 20 %). The objectively measured improved cushioning was also rated highly by the wearers. Conclusions: The present study shows that long-term improvement in cushioning properties of safety shoe footwear may be achieved by altered shoe construction. This improvement in cushioning is also rated positively by the footwear users. This may lead to better compliance in workers obliged to wear safety shoes.