I've been thrifting all my life. And since moving to my present home, I've found the thrifting fabulous (unfortunately not as fab as some of your experiences; the top end of what I find tends to be Brioni, Canali, Belvest, Zegna, Ferragamo, Allen Edmonds - awesome stuff, sure, but not what some of you have scored.) So, it's hard to pick one item that's tops. But, I can tell you the rarest.
About a year ago, I found a pair of split-toe, 4-eyelet oxfords, with the big squared toebox that was fashionable a few years ago. Nice waxy-finished leather, as well as some unusual SQUARED perfing. Not perfect shape, but still, very nice shoes. Imagine my amazement when I looked at the insole and saw the maker's mark of ... JIMMY CHOO. Yep, the designer who the ladies can't seem to get enough of, but only the ladies.
I actually didn't buy these when I spotted them. Frankly, I wasn't sure they were real. Jimmy Choo for men sounded like some kind of bizarro, half-assed chimera cooked up by idiots in a back alley in Shenzhen or wherever the Chinese counterfeit designer shoes. The next day, I went back and bought them.
I went to the Jimmy Choo boutique in my city and chatted up the clerk. She was sweet but clueless, and there were no Choo shoes for men anywhere in sight. I found a contact form on the Jimmy Choo website and emailed their offices directly.
Next day, I got an email response from London. (I'm paraphrasing
"In the beginning, Jimmy offered a line of men's shoes." So they weren't a chimera. And in hindsight, why counterfeit something almost no one knows ever existed?
Oh, the price: FOUR BUCKS.
Shoe porn attached. (The last one is actually a comparison shot with one of the Choo shoes next to an A-E "Bradley," a somewhat-clunky split toe that looks sleek next to this one.)