I have some booties which I wear out under boot cut jeans. About a 2 1/2 inch heel.
I remember seeing some short videos FastFreddy posted showing his version of stealth mode - stilettos and a quite high heel, under boot cut jeans. But can't seem to find the thread again.
I think I like the idea of stealth-ish mode. Potentially you could do heels, ladies jeans, ladies polo or blouse that looks like a shirt.
A small statement towards clothing freedom perhaps, but you know for yours