The aim of this experiment was to provide insight into the immediate influence of both semi-custom insoles and knee sleeves in recreational male runners/athletes suffering from patellofemoral pain and also to explore the association between the extent of patellofemoral pain and psychological wellbeing. Experiment 1 examined 17 male recreational runners with patellofemoral pain, in semi-custom insole and no-insole conditions. Experiment 2 examined 13 male recreational athletes with patellofemoral pain, undertaking run, [Formula: see text] cut and single-leg hop movements in knee sleeve and no-sleeve conditions. In both experiments, motion capture and ground reaction forces were collected, allowing kinetics and three-dimensional kinematics to be calculated alongside patellofemoral joint loading quantified using musculoskeletal modeling. In both experiments, patellofemoral pain symptoms were examined using the KOOS patellofemoral pain subscale and psychological wellbeing using the COOP-WONCA questionnaire. The findings from both experiments showed that pain symptoms significantly predicted psychological wellbeing ([Formula: see text] in experiment 1 and [Formula: see text] in experiment 2). Experiment 1 showed that orthoses significantly reduced tibial internal rotation range of motion (no-[Formula: see text] and [Formula: see text]) whilst also increasing the peak knee adduction moment (no-[Formula: see text][Formula: see text]N[Formula: see text]m/kg and [Formula: see text][Formula: see text]N[Formula: see text]m/kg). The findings from experiment 2 revealed that the knee sleeve reduced the peak patellofemoral force (no-[Formula: see text][Formula: see text]BW and [Formula: see text][Formula: see text]BW) in the run movement and the patellofemoral load rate in the cut movement (no-[Formula: see text][Formula: see text]BW/s and [Formula: see text][Formula: see text]BW/s). Overall, the findings confirm that pain symptoms are predictive of psychological wellbeing in recreational male athletes with patellofemoral pain. Furthermore, the findings suggest that both insoles and knee sleeves may provide immediate biomechanical benefits in recreationally active individuals with patellofemoral pain, although when wearing insoles this may be at the expense of an increased knee adduction moment during running.