By "winners" I mean those items that you reliably reach for again and again and again, so eventually their cost per wear becomes minimal.

They MIGHT be basics, but then again, they might not.

My new consignment jacket cost me $35, but already the cost per wear is less than $3. That's right! In just a few weeks, I have worn it that many times!

When I bought that jacket, I was vaguely hoping to find some sort of tweedy jacket this season, but I didn't see it as a "must have" purchase. I happened to see this one; it seemed to be a good price, the fit was right, and I imagined that I would probably get some use out of it. And I figured that at the price, even if I didn't wear it, it wouldn't be a catastrophe.

I had NO IDEA it would become such an incredible workhorse!

If this jacket had been ten times the price, it still would have been worth it to me.

In retrospect, I see that this jacket shares some features with the jacket in one of my "favourite outfits" that I described to Mrs. Eccentric. http://dashingeccentric.blogsp.....-case.html

It is a textured wool jacket, fairly short, quite fitted. These seem to be qualities that appeal to me for some reason.

But how can we identify items like that in advance? Do you have strategies? Or is it sort of like falling in love...a certain amount of magic is involved?