Stilettos are best worn....

Depends on the stilettos - open toed or closed toed -, the rest of her outfit and her mood, I guess.

Depends on the rest of the person attire as required by the ocassion it can work either way or look stupid and cheap either way as well. Like any other item of female clothing the woman wearing it has got to be able to carry it off. High heels need good balance to work

By women in stockings.

By mannequins. LOL.

I don't wear them, I can't walk in them.

in a sheath until you're ready to stab somebody