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$3 V neck grey t-shirt from H&M with chest pocket (on sale). I got it like 5 years ago and it is still the best fitting tee I have ever owned. It is the right weight (not too heavy or too thin). I deeply regret only getting one because I never found the exact same shirt again from there. If I could back in time I would have purchased 25 and be set for life.
Used leather jacket with ripped zipper at a Salvation Army store. $10. + another $5 to have my tailor put on a new zipper. That jacket's still going strong after a decade and it effing rules.
Damn, I overpaid. I paid $20 to have a new zipper put in my vintage leather jacket...