Another super thrifter here!
You look gorgeous in that herringbone sweater, Roxanna. I love all your pieces.
I've been designer thrifting since I was a kid and unfortunately once you start you can't go back: you get so used to high quality items that shopping in cheaper stores is unsatisfactory, and so accustumed to low prices that paying more than 20 dollars for anything feels like a waste of money. It can really put you in a shopping bind.
My latest score was a brand new shirt from The Row for 1 dollar at a rummage sale. It's worth at least 300 or 400 dollars. Still debating whether to take the tags off and wear it or sell it online, haha. It's a lovely cashmere/modal top with impeccable tailoring, made in USA. Sometimes I take it out just to admire the workmanship!
You are really smart to go for the Italian made clothing. When I lived in Italy I picked up several vintage pieces in the thrift markets and years later they are still going strong and look beautiful.
I think thrifting is certainly a lifestyle thing, and you have to enjoy it to do it well. There are also some skills you develop on the way: how to spot the good stores and sales, how to check used clothing for defects, how to recognize good brands and fabrics, how to buy on the internet and not get cheated, etc. It's personally very rewarding, though. Most of my friends don't like thrifting, but whenever I go thrifting, they beg me to take their wishlists and pick things out for them. It's double fun!