I would say the meaning of vintage has changed to me over the years. I discovered it through my mother taking me to a vintage shop in London on a trip there around 25 years ago, because she collected vintage costume jewelry and knew the shop already - and a little later, I started going to second hand shops with my best friend, where she was buying cheap work clothes. I was attracted mostly to the bling - evening wear. All my princess dreams come true! And it was a time when you could buy a 1960s evening gown for 20 Euros, before vintage got trendy. Over the years, I started buying vintage day wear at second hand shops, and I started looking for second hand and vintage shops on my travels. At the same time, for any "dressy" occasion I would go full on, trying to do the period look, wear my evening wear... and I discovered the VFG and these forums and I got more and more into vintage for truly every day. Nowadays, I shop vintage and second hand almost exlusively and sew my own things with vintage patterns and vintage or modern fabric. I'm not trying to achieve some kind of period look anymore. I just wear my own style that I like and I buy things that I feel are "me", no matter which era - the only exception really is underwear and the like. I may wear a 1940s suit jacket with a 1960s blouse and modern pants, or a 1940s dress with an 80s jacket and second hand shoes. What is important to me today is that these things reflect my personal style, that they are unique, I feel totally comfortable in them and they are mostly of superior quality than what you find in most shops (and for a better price!) - and it is also a sustainable way of having a fabulous wardrobe. I have left fast fashion behind me and I am glad of that. I'm also not trying to keep up with any trends. Oh, and I get a total kick out of getting a compliment every time I wear a certain 1970s polyester dress for a business occasion and I know I got it for 20 bucks in a weird thrift shop and thing to myself "if you only knew", or somebody goes "this looks like Versace" - uhhh, no, it's a 70s polyester skirt that cost a fraction of anything Versace...
I can't really come up with stories of previous owners. One of my best/favourite finds was this dreamy 1950s silk cocktail dress that cost me the equivalent of about 15 Dollars. I went to a hipster flea market in a part of my city (Zurich) that I don't go a lot to, because I was looking for a specific second hand thing that I was hoping to find there. I did not find that, but of course I browsed the stalls. It was December, it was in a half-open tent, there was nowhere to try anything on - and there was this dress on a rail between other less execiting and newer clothes. I took a chance for the price, fixed a few small seams (it's beautifully made - more or less couture quality, but no label anywhere) - and it turns out it fit perfectly.