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How to learn to walk in heels
How I did it: I basically just actually forced myself to wear heels. It was mostly my fear of wearing heels that made me feel like I didn't know how. Now, I still don't know how to walk in what I call "Emma Watson heels" (like, those crazy high heels that also have the platform on the toe?), but I'm not worried about that. And I am still deathly afraid of stilleto heels... but I think I'll stay that way. Those things are just not practical.
Lessons & tips: Just force yourself to wear them, and force yourself to walk. You'll get the hang of it. I got advice once to roll-step (from marching band), but I'm not sure how well that works... because I never have decided that that's the best route.
Resources: My mom, for providing the heels that I now own. My color guard instructor, for sharing stories of when her guy friends wore high heels.