Mmmmm, pie....
I think this is a hard question. It depends on the item, and my frame of mind, and where my style is headed. I try to ask myself now, when I am struggling or ambivalent about a new item, if it's congruent with my clearly defined style or not. For example, I just got the J. Crew hacking jacket in that beautiful bright blue. It's a tall size, so the sleeves are actually long enough, and the fit was perfect. But...I felt sort of ambivalent. I don't like the buttons (too traditional) and I started trying to pair it up with some of my things, and realized that for me, it was just too traditional/classic overall. So, not in the direction I want to be headed right now, so back it goes. If it's challenging but still headed in the style direction I want to be headed in, then I can work with it.
