Most Helpful Girl
"my name is [name]. i like pizza, long walks on the beach, and occasionally wearing women's shoes."
if someone told me that, i'd totally be okay with it. as long as you are upfront about it, i don't see why it would be an issue.3
Most Helpful Guy
It's always hardest to talk to the ones you're closest too. If you tell them up front that you are nervous and about to tell them something that makes you vulnerable to judgement, but don't want them to have a lower opinion of you, most will expect something far worse (child porn or something) and be relieved to learn that its only this. I would try to approach each individually or in a small setting and tell them what you just said above. After you have told several, you can start wearing the shoes around them. Then as you become more comfortable, it will be less of an issue.
I agree that you shouldn't just show up at their house wearing them.1