Super WORN Vintage?

There's talk that pieces like you see above are a slap to the common consumer. Where those with means will pay more for something that's been used, heavily. Interestingly, there's something there that money can, sort-of, buy (maybe). For example, a worn old tee shirt probably has a story to tell, likely many stories of days and nights of wear. A-la your 'favorite shirt' that you've worn everywhere, forever. The confusion starts to build when somebody buys a distressed piece and wears it pridefully, implying the wear is their own and was done so over time with experience. What does that say? I was there, and here, and I did stuff, and here's my proof? Or is the soft feeling of naturally worn cotton just perfect for a hot summer afternoon? I guess that's the mystery.