The integration of actuators into wearables to support haptic output and shape change provides an alternative to overused modalities like audio and video that allows a tighter coupling of feedback to body parts. Adopting a research-through-design approach, we report on six design explorations on how actuated clothing can support users to learn a movement skill, e.g. for sports or for the purposes of rehabilitation. Our exploration of actuation in wearables focuses on the aesthetics of form and of interaction, especially in relation to expressiveness and supporting how the user relates to other individuals. In this article, we discuss challenges and design potentials related to user experience and aesthetics of actuating wearables in this context.