L67 -- very smart to think of keeping a few non-essential, slightly-past-their-prime pieces on hand to mess around with. I may steal that idea.
JB -- my feeling is that when they "come back in style," the chances that the original version will still look fresh are slim. What has been your experience? Does it work well enough that it makes you glad you waited?
SF -- maybe you could pass along some tips to those of us who go in the other direction.
Az -- "I can think of quite a few things I've purged over the past few years that I wish I'd held on to." Me too, girlfriend. Me too.
Angie -- wish I had some of my mother's items too. She's tall and straight, no curves, so not much of her clothing would work for me, but she had things like my dad's oversized varsity sweater that I would kill for now. (I got that one, by the way -- wore it to death through college, when my look was very "thrift shop". Then I lost track of it in the bustle of young adulthood. So sorry now.)
Anne -- I was thinking that too. When my budget was very tight (see "thrift shop" comment, above), I would get panicky over letting anything go, for fear of being unable to afford to replace it if and when I needed to. Something helpful I learned from "Flylady" (American housekeeping coach), though, was to learn to trust in yourself. Let things go, she says, and trust that if you need to replace them in the future, you will find a way to do so.
I may have learned that one a little too well.