Abstract: Free-play is key in the cognitive and emotional development of children. Yet, opportunities for free-play are diminishing. Previous studies have designed digitally augmented open-ended toys and playgrounds to encourage free-play. Wearables, despite their rising popularity and potential for fostering free-play, have received scant attention in research on digitally augmented free-play for children. This paper shows how four qualities of wearables (individuality, natural interaction, ubiquity and intimacy) were incorporated in the design of three wearable playful accessories aimed at school-aged children (age 6-12), and how these qualities enabled the accessories to foster rich and diverse free-play experiences. The results open up design opportunities that can potentially help wearable toy designers and researchers to create future playful wearables