Wow this is a good thread!
I toss, I just realized as I went through it in my head, almost ALL the items I buy on sale. Oh good lord. I should stay away from sales ... Or stay away from them unless I'm feeling so fabulous that day I'll be immune to bargain hunting thrills and chills. Maybe get on YLF right before I go :p
But! I love my thrifted items. I almost never give them up until they've been worn through. They are the bulk of my beloved items. When I buy more expensive pieces I tend to wear them because I feel like I should an they look fine, not because I love them. My thrifted items I love. Why on earth? My only theory is that I buy more boring and quote unquote versatile when I'm paying more. And the items bore me. There's some truth I that I think.
Still, thrift-and-tailor shopping is my tried and true strategy. You get variety of time period and brand and nothing is too trendy or clone-like and everything fits because you spent the money to make it fit.