It basically meant young people who worked 2 shifts at the coffee shop and the occasional bartending shift when they were lucky enough to get one so they could afford to drink cheap beer and go see a lot of bands and/or be in one. Add a bit of a certain kind of fashion - beards, tattoos, skinny jeans - and you had hipsters. A key feature was that they worked shit jobs and didn't have any money. Then somehow it morphed into some version of "trustifarian." And, yeah, maybe some New York and Bay Area hipsters were trustifarians, but not really the ones in the rest of the country. We get it, New York, no one is really poor there anymore. Well they are in the rest of the country. Then in its final evolution it just became a synonym for "the young Yuppie in my head who has more money and more fun and more sex than I do wish he would get off my lawn." Basically, it means a fantasy version of The Kids Today who are all rich and lazy and hedonistic.
For the olds, we get it, you (#notallyou) hate the Kids Today and their regular reminders of your mortality and all of the opportunities you think you missed. But the word "hipster" has become utterly meaningless except as some weird projection onto all younger people.
