Wow - so, so many thought provoking responses and comments here. Thank you for your replies.
AJ has really hit the nail on head with her question "Is it worth it to spend money on a quality, trendy item that has a high happiness factor?" It's almost a question of WHAT COUNTS FOR MORE IN A PURCHASE - LONGEVITY OR HAPPINESS? Of course, most of the time, we'd like both.
I also am struck by Caro's comment "Sometimes something like these trousers makes everything else we wear seem modern & a little different & I think that's a good thing." Maybe the cost of a pricey item is justified by the way it makes you wear your current closet items. The quantity of items you purchase decreases BECAUSE of the one pricey item you bought and so overall, your budget remains intact but your wardrobe has been refreshed.
Anna has also made an extremely poignant comment "One thing I discovered when I lust after a particular item that is expensive, I have a habit of shopping around it. Often times I end up spending more money than the original item." I've done that and you end up broker and still unhappy because you don't have the item you fell in love with.
I am not one who has ever tracked CPW, other than loosely in my head from time to time. I know this works very well for many YLFers and I'm always in awe of those who actually calculate it. But as everyone knows and Angie has pointed out, I shop and dress with emotion and from the heart so I suspect CPW wouldn't work for me at all.
I'm not sure I'm going to get the pants, although I'm going to go to the local boutique that I found in my home town that carries Eileen Fisher and see if they have them to try on. I have the feeling my shopping habits are changing significantly - I thrift much less than I used to and even there, have become much more discriminating about what comes home with me. I'm not going to go crazy and pay exorbitant prices for things that I can get for less with equal quality. But at the same time I'm realizing there are things I am willing to pay more for if it is the right item.
Going back to read your replies again and do some more thinking...