Wearable exoskeletons are emerging technologies for providing movement assistance and rehabilitation for people with motor disorders. In this study, we focus on the specific gait pathology dropfoot, which is common after a stroke. Dropfoot makes it difficult to achieve foot clearance during swing and heel contact at early stance and often necessitates compensatory movements. We developed a soft ankle exoskeleton consisting of actuation and transmission systems to assist two degrees of freedom simultaneously: dorsiflexion and eversion, then performed several proof-of-concept experiments on non-disabled persons. The actuation system consists of two motors worn on a waist belt. The transmission system provides assistive force to the medial and lateral sides of the forefoot via Bowden cables. The coupling design enables variable assistance of dorsiflexion and inversion at the same time, and a force-free controller is proposed to compensate for device resistance. We first evaluated the performance of the exoskeleton in three seated movement tests: assisting dorsiflexion and eversion, controlling plantarflexion, and compensating for device resistance, then during walking tests. In all proof-of-concept experiments, dropfoot tendency was simulated by fastening a weight to the shoe over the lateral forefoot. In the first two seated tests, errors between the target and the achieved ankle joint angles in two planes were low; errors of <1.5° were achieved in assisting dorsiflexion and/or controlling plantarflexion and of <1.4° in assisting ankle eversion. The force-free controller in test three significantly compensated for the device resistance during ankle joint plantarflexion. In the gait tests, the exoskeleton was able to normalize ankle joint and foot segment kinematics, specifically foot inclination angle and ankle inversion angle at initial contact and ankle angle and clearance height during swing. Our findings support the feasibility of the new ankle exoskeleton design in assisting two degrees of freedom at the ankle simultaneously and show its potential to assist people with dropfoot and excessive inversion.