I posed this exact question to my boyfriend recently, as I often do, (usually before 7 am, which I know is really not fair.) But anyway, sometimes it's a hard choice and often I give up on a "look" because I don't have the "right" shoe for it, (Will you ever be found perfect black flat?) On this day it went something like this:
After several pairs had already been tried and passed by...
Me: How about this one?
He: Yeah, that's probably the best one.
Me: Wait...what about this one?
He: Hmmm...it's ok, the other one might be better though
Me (looking in mirror): Nope, I'm going with this one.
He: But the other one is just...there's just a little more something too it...
Though usually I agree with him, I wore the boot. I wasn't feeling all that well and I knew I had some running around to do that day, and the heel wasn't as high, blah blah blah. So maybe I'm an emotional shoe wearer...which would you have chosen?