Gender issue is one of the essential topics in issues-based art curriculum with the aim to promote a democratic and just society. Choosing everyday items that students have been interacting with as a topic to discuss gender issues can improve students’ engagement in class. For instance, taking dolls and their packaging as a starting point, I discussed gender issues with middle schoolers in a Saturday Art Class located in Houston, TX. In this article, firstly, I reviewed the literature of feminist curriculum in art education and culture jamming. Secondly, I shared several middle schoolers’ deconstructive works of art. Finally, I provided suggestions regarding how to foster students’ deconstructive skills in the long term.