well ironic means paradoxical, but hip, can mean pretty much whatever anyone wants it to mean. ironically hip? its certainly ironic, some of the things that have come to be considered hip.
Hip means hip and ironic means ironic. But I think you're talking about some sort of hipster thing that neither the previous posters nor I am familiar with - but I hope you're not. If you are, please let us stay this ignorant way.
hipster and hip (as in hippie, though i suppose the derivation is populist, but then populist isn't always popular or at least not always dominantly so), are rather different animals, as well. perhaps not totally exclusionary, but nearly so if not. people do such silly things with words, and then make blind assumptions on the basis of doing so. at any rate, that is precisely what the previous posters appear to me, to have been doing.
Hip, simply mean fashionable, there's nothing more to it. If hippies are no longer fashionable, one can guess that they were when they first became prevalent. Not to get into the meaning of the word ironic by itself, but when one qualifies as what so many consider both hip and ironic, the predictability of that person is sincere. The irony attempted there is such that mocks all the cares of modern people except those cares that are particularly fashionable at the time. The movements towards equality or world peace, for example, will rarely be mocked. Their irony is a shallow cynicism. Shallow because such people are generally not overly sensitive to the effects of modern living, and therefore do not wish to speak against their own comfort, but rather wish to speak against all that would interrupt their current comfort level, such as any ideology that emphasizes challenging oneself beyond the challenge to remain fashionable and therefore well-liked.
Reagan closing mental help possibilities for the mentally ill in California was ironic when he lost his mind. Hep was the same thing as hip back in the 30s-40s, usually reserved for dope smoking musicians. Hip fit better after that writer from the SF Comical called the 60s folks hippies. Maybe hip-ironic was when I saw a carload of girls in a new Mercedes park it blocks away from where hippies were hanging out and then joining them. To be hip, I guess.
see the last paragraph of this review by Roger Ebert in 1996. rogerebert.com/review/kids-in-the-hall-brain-candy-1996 Maybe it will spur you to help me understand the gist of what hip and ironic is.
Hip and iconic is a phrase that's easier to define. (actually I dislike the term 'iconic' which gets massively over used these days IMO) I'm not sure when irony became hip, Probably always was when used in the right context.
