For clothes, I like investing in some good quality, classic pieces. Like a $200 jacket that will never go out of style. And then I'll pair it with a tank top from the dollar store.
About 20 years ago, I bought a high quality ladies skirt and jacket combo in a classic style, that I paid an outrageous amount for, but I'm still wearing both pieces.
I don't mind paying more for pieces like that, but I also don't like paying $60 for a friggin' white or black t-shirt. Dollar store or thrift store for stuff like that.
I love vintage stuff, too. You need to shop around for those deals - vintage can be over-priced.