i have never really went by what was in/out. if i put it on and i like it...i go with it.
having i often get the "what the hell is she wearing" looks when i go out, but then in a year or two, after seeing it on tv or film, those who were saying "what the hell is she wearing" often come back and ask me..."remember when you had that *blah blah* on? how do i get that look?"
so i say if you put the boots on with the pedal pushers and it still looks good to you -- rock it!