hiddenheels

I would like to "go big" once before the holidays. Would like to wear a mini-skirt with 4" knee-high almost stiletto boots, male stuff on top. I won't pretend to be a woman, don't want to, just want to wear what I want without pretense. Love the outfit I have in mind. However, although I've gone out in similar outfits in the past a few times, the boots were combat boots, or were hidden underneath jeans. So I think this one is a bit more daring. Right now, just thinking about it gives me serious anxiety. Sometimes I don't care, and just go for it, sometimes I'm completely up in my head, and can't get past my ingrained cultural role and what should be my "correct" presentation. Does anyone have any tricks on overcoming this? Is it just practice-makes-perfect?