I was jocking in another post that my husband encourages me to wear what I call "executive style": suits, stiff shirts etc. Which is a style I like (minus the stiff shirts), but not really what I usually wear, or the best choice for my lifestyle. I find this dichotomy quite interesting.
Another funny episode was when a colleague was getting married, and we were looking at a catalogue of wedding dresses. One of my colleagues saw a lace dress and said something like "this will be your wedding dress", which couldn't be more wrong, as it's really not my style.
And now that I think about it, my mom keeps thinking I only wear flat shoes, which couldn't be farer from truth. Who knows?
Now back to you: have you had cases where your style was not understood at all?