The paper addresses the challenge of balancing the tension between a problem solving attitude in the design of assistive devices, with an ethical, aesthetic and cultural approach to design for people living with a temporary or permanent impairment. The topic is developed presenting two design cases. The first case is a suite of smart jewels tailored to the needs of people with hearing impairment (Marti & Recupero, 2019), (Quietude, 2019). The jewels sense environmental sounds (e.g. the doorbell, an alarm, someone calling, a car horn) and notify them to the wearer through different modalities (light patterns, vibrations, shape changes). An App completes the system allowing the deaf person to record personal meaningful sounds and set preferences for their notification. The second case is an orthodontic facemask for children designed as a 3D printed super-hero mask made of biocompatible materials (Marti et al., in press), (SuperPowerMe, 2019). It is associated to a game where a superhero avatar wearing a similar facemask gains power by progressing in an adventure. The design cases represent examples of permanent and temporary impairment that share fundamental features of the user experience: the stigma associated to hearing aids and orthodontic facemasks alters self-image and self-esteem of people affecting all aspects of life. The cases show that design can promote a cultural shift by transforming assistive wearables into beautiful, playful, gender-appropriate accessories.