I used to be a vintage fashion dealer, so I have owned a lot of valuable clothing that I paid a pittance for. The thrill for me was the hunt so most of those items were worn a few times and resold. This is the most expensive item of clothing I have ever bought and kept. It is a 1930’s silk velvet evening gown with bell sleeves lined with a band of gold lamé. I believe I spent $300 on it in the eighties. I wore it as first as my prom dress in 1989 and then as my most special evening dress for about ten years. I wish the picture was better. I still have it but it was beginning to develop hanger r The most expensive outfit I ever worn (besides furs, which are necessity in Siberia where I am from) would be the dress by Alain Manoukian that I bought for my university graduation party. In 2010 it cost about 250 USD. It was (is, still have it) a soft shell jacket I bought for a backpacking/train trip to Europe in 2007. It was about $250. I got one for my husband too. He liked his more than I liked mine. Can’t remember the brand now but I definitely fell for the marketing. It was supposed to be a lightweight all weather jacket that would keep me warm but still breath but the underside of the face (wasn’t lined) felt very clammy on my skin and I was forced to wear a long sleeve tee to avoid contact with my skin.