That's an interesting reaction - primarily because a sense of entitlement, to me, seems like neither necessary nor sufficient conditions for being either hip or slack. It also seems like you're suggesting that hipsters did not exist until recently, which strikes me as untenable.
Fashion takes work...too much work, in my opinion. Perhaps you say this because they both drink lattes?
It's also an inaccurate characterization of the "slacker" literary genre. The gen-X "slacker" persona was always more about the cultural malaise caused by the dramatically lower lifestyle prospects afforded to the post-boomer generation, than it was about being "entitled" (for those who are interested, go read "Generation X" by Coupland to see the origin of the genre. It's also a really good book.) Hipsters have been around for a lot longer than that (since the Beat Generation, at least), and are more defined by hedonism and rebellion than by disillusionment.
While I don't think that these sorts of stereotypes are terribly precise (or incredibly useful), it is sort of interesting that younger generations seem to be lumping together gen-X-ers, hipsters, and Holden Caulfield together under the label of "entitled". If you ask me, the current generation of college kids are far more "entitled" by any conventional definition, so it's a curious choice.
The destruction of Europe and post-war prosperity and the advance of technology has led Americans to grow progressively more entitled. It's no wonder kids today lump it all together, because in general any American under 60 is way more self-entitled than is warranted under current global conditions.
Well, they are entitled. Its their world. its their life, they have been educated of such high ideals as democracy an human rights and they are richer than any previous generation.
Fashion takes work...too much work, in my opinion. Perhaps you say this because they both drink lattes?