Such wonderful responses! Thank you all!
MamaKate, you are wakening me to the wisdom of spending on a belt. I have found it difficult to part with $$ for belts in the past, but your example shows that the right belt might be in a person's wardrobe for YEARS and why wouldn't I shell out some $$ for it? The cost per wear is much cheaper than shoes!
Sylvie, I love your list.
Makrame, I am certain that quality is important for me, too. I can't think of an item that I truly adore that is cheaply made. It might have had a low purchase price, but if it's not well cut and constructed, I will fall out of love with it very quickly.
Mo and Londonkiwi, ease of care is a factor I hadn't even really thought about, but you are right; for many items this is crucial, especially casual wear items. I guess a wrinkle on the "ease of care" idea would be the whole concept of how the item fits with your actual life; if you have pets, a pair of pants that pick up lint like nobody's business or a sweater that your cat will snag before you can say HelloKitty are not likely to be daily wear items.
Londonkiwi, your point about some big ticket rarely worn items being "winners" is well taken. I couldn't agree more. I have a dressy skirt like this; I wear it twice or three times a year but I have had it for three years now and will probably have it for at least another three. And every time I wear it I feel terrific. So although it cost me a great deal, I never feel bad about having spent that money.
Nancylee, I think you are really onto something with the "missing link" theory. And sometimes we don't even fully understand that we have a need until we find the item to fill it.
Helen, your list of winners sounds heavenly; having seen your pics I was imagining you in all those colours. As for the Naturalizer shoes, they make some great styles and lots of people on this board are super-satisfied customers!
Anya, it is items like that polka dot skirt that make me wonder. I think my jacket falls into that category. At first glance it's not exactly a wardrobe staple...and yet, it becomes one!
Rae, you caught me out on the black bag issue! I have been thinking that exact thing! So now I know that a colourful bag would be a winner for me, thanks to you! And I think my jacket, had I known, fits into the "variation of something I already love." Plus it works with many other items in the wardrobe.
Angie, that's it - the items that always make us feel our best. The funny thing is, we can't always tell in the fitting room (or even back at home) if an item is going to do that. Or at least I can't!
Aida, I think pickiness is far more important than I ever realized. I used to always "make do" with whatever I could find. I am learning that it's false economy. And Sharon, Elly, Heather, you are so right...it's how the item makes us feel that matters most!