Something just clicked in my brain as well because of this thread. I'm beginning to wonder if most of us have an instinctive, innate style
that exists, even if we can't fully articulate it even to ourselves. And, an item, somehow has to tap into that style sense if it is to become a "classic" for me.
Give me someone else's version of a LBD, or a jacket, and I can feel (and probably look!) like I'm wearing a costume. Give me my version and I can't conceive of my wardrobe without it. My LBD is a pair of black, cigarette-legged pants, Janet's trench might be her blue leather moto, and so on. Maybe assembling a wardrobe of "classic" pieces requires reflecting on our individual representations of the famous items on the list instead of running out to buy the actual icons?
Because, to be truthful, I can't see myself ever wearing a pair of ballet flats, or a beige trench, without feeling like I was dressing for someone other than myself.
ETA: I just read Angie's distinction between "classics" and "workhorses" but I'm sticking with my idea that the term "classic" can refer both to the icon (a tan Burberry trench, for example) and a more free-flowing representation (Janet's blue moto) which, IMO, is more likely to be a workhorse since the representation fits one's personal style. My rationale is that without being able to use the term both ways, talking about including "classics" in one's wardrobe leads to that lemming-like behaviour where everyone thinks a functioning wardrobe ought to include a beige Burberry look-alike. Classics are important for all of our wardrobes, but they don't have to be the icons as long as they fulfill its function and spirit.