One of the purposes of footwear is to assist locomotion, but some footwear types seem to restrict natural foot motion, which may affect the contribution of ankle plantar flexor muscles to propulsion. This study examined the effects of different footwear conditions on the activity of ankle plantar flexors during walking. Ten healthy habitually shod individuals walked overground in shoes, barefoot and in flip-flops while fine-wire electromyography (EMG) activity was recorded from flexor hallucis longus (FHL), soleus (SOL), and medial and lateral gastrocnemius (MG and LG) muscles. EMG signals were peak-normalised and analysed in the stance phase using Statistical Parametric Mapping (SPM). We found highly individual EMG patterns. Although walking with shoes required higher muscle activity for propulsion than walking barefoot or with flip-flops in most participants, this did not result in statistically significant differences in EMG amplitude between footwear conditions in any muscle (p > 0.05). Time to peak activity showed the lowest coefficient of variation in shod walking (3.5, 7.0, 8.0 and 3.4 for FHL, SOL, MG and LG, respectively). Future studies should clarify the sources and consequences of individual EMG responses to different footwear.