I understand fashion quite well, and more importantly, I understand fit and know when something flatters and when it does not.
However, these days my figure is shot to hell and there just doesn't seem to be much point most of the time in spending for nicer things that are more likely to be most flattering, or taking the time to alter them. I saw a lovely silk blouse on clearance yesterday and passed on it, because I know that my 2 yo would ruin it in less than an hour. Mostly I live in chinos and sweaters right now, as my workplace is quite casual.
I am bad about tossing out clothes that still fit and flatter, even if they are out of style. I've got oxford shirts with dropped shoulders in my closet still. That's what parenthood will do for you -- I just don't have the time to shop carefully anymore, so I hang onto basic things that still fit. I was just asking myself the other day if it's really necessary to go from hip-length to longer tees, LOL.