The old saying goes, "You can't understand someone until you've walked a mile in their shoes", or in this case, "heels". To punish my prejudiced relatives for gossiping about my supposed sexual proclivities, I asked my female-presenting friends to submit pictures of themselves that I would then recreate to post on my social media. If my kin wanted to talk about me behind my back, I wanted to make sure they had something to talk about. Then something curious happened... not with the supposed proclivities. Get your mind out of the gutter, you scoundrel. What began as a light-hearted revenge attempt toward my bigoted family ended up growing into a deeper understanding of perceived societal gender roles, and the biases that surround them. I began to ask why we base ourselves on the outdated concepts they present. How are these misconceptions allowed to be fostered in the present day? What can we do to stop it? This book is a slice of life account, chronicling my journey of self-discovery as I wrestle with these questions and others, all while looking absolutely fabulous.