Some humiliating outfits you can think of so I never...?

Don't embarr yourself, embrace yourself and accept what you are. You only live once, enjoy yourself. Humiliation will only make you feel bad, and you should never make yourself feel bad on purpose. Go nuts friend - polish, heels - whatever you want. Screw society and find some friends who will accept you - head held high. And before anyone jumps all over me, saying I'm a crossdresser or whatever, I'm a 40, married, and a mom.