Sasha I think it is really important to find someone who likes you for being you, but it's also fun to dress up and be treated special when you go out. I get wanting to avoid certain looks and not going crazy with make-up, but, there is still a middle ground. If nothing else, wearing a skirt with a frumpy top just seems weird.
I've only worn home made semi fake thigh bands, but I think they give you a sexy gait similar to wearing heels. That being said, if you are comfortable in heels and you have heels that give you good control, you might want to wear them to give people a visual indicator for why you are walking the way you are.
Good luck with your trial run!