It is indeed hip, not cool, that is relative. If you're hip, you're hep to a scene, but to someone who's not down with that scene you're just square. But if your vibe is cool it doesn't matter if the cats don't dig; you're cool with that too.
Glad I could help.
I think you are right about "hip" in that it is absolutely relative to a scene.
But I suspect that it is right that "cool" does depend on some cultural norms. If I disagree about James Dean being cool, how would I respond? Well, you'd exhaust the reasons why he is cool, and I'd have to say - "you think that's cool? No, cool is ..." I'd target the definition. There is probably some "character" to "cool" which stays the same across all uses. This is Kaplan's notion - for example, the character of "I" is something like "the speaker of this utterance" despite the fact that it changes reference on each occasion of use. Similarly, "cool" might have a character like "exemplar of ..." but the rest of the content is filled in by context (e.g., cultural norms). That also leaves open the door for some traits to be "core" cool, like calculated disaffection, but others to be culturally dependent, like wearing a leather jacket or riding a motorcycle.
Alas, given the range of speech acts we use "cool" to perform, I'm not sure how reliable intuitions are on the matter! Nevertheless, words are cool ^^
It's probably right that hip must be related to something. I'm not convinced that it need be a "scene", in part because I think you would need to discuss what qualifies as a scene, and then there's the question: are all scenes capable of having someone be hip to them? If not, why not?
Hip seems to be a mode, relative to a given paradigm or schema, whereas cool is a quality more closely related to a person's character. One can be a cool cat, regardless of being entirely unrelated to a given scene or subculture.
Perhaps hip is relativistic, and related to a changeable inconstant, whereas cool is mechanistic, related more to the upness of a person, which is itself relative to some normative downness? Perhaps.
There is probably some "character" to "cool" which stays the same across all uses.
Indeed.
And somehow, sunglasses always assist. Quite odd, that.
I'm not sure, but I think I may be speaking from the mossy origins of these terms. As originally perceived during the Beat period, at least by me and my cohort, Cool was something achieved by open-mindedness, which naturally led to Hipness (literally awareness). James Dean, then, could be imagined to be objectively Cool because disaffected as result of lofty awareness. Sorry if this is an intrusion of perceptions of the Ancient.
Hip and Cool are two sides of the same coin.
Hip is active, passionate:
"Keenly aware of or knowledgeable about the latest trends or developments."
Cool is passive, reflective:
"To calm down; relax."
Hip is knowing when to speak with passion. Cool is knowing when to shut up.
"Keenly aware of or knowledgeable about the latest trends or developments."
I refuse to acknowledge the ultimate authority of that definition. I see no reason that it needs to be the "latest trends and developments". One could be hip to Coleridge, and he's hardly the latest development. And if you aren't hip to Whitman, then I have no use for you. Good day to you, sir.
> I have no use for you.
If you did have a use for me,
what would you use me for?
This may just be a product of where and when I grew up, but I feel that anything below about 60 degrees Fahrenheit is cool, down to about, say, 40 degrees, at which point it becomes cold (depending on wind-chill, direct sunlight, etc.) Above 60 to about 75 is warm, and above 75 would be hot.
...what? Oh. Guess I'm not hip to this scene.
> ..what? Oh. Guess I'm not hip to this scene.
One thing is for sure:
Your web site
( http://www.variedperspectives.com/ )
is as hip as can be.
Cool can mean a million different things. I rarely hear people use the word hip, but I always figured it meant the same thing as cool. Cool is just a cooler term than hip. 
Thanks, Philo! Maybe I should start updating it more than once a month....
Can cool and hip be used back to back in the same sentence? As in , "He's a real cool hip cat, or hip cool cat." Wouldn't the coolness counteract the hipness making it a double positive which in turn make the once cool cat or hip cat in to some other type of animal?
Cats are mostly cool.
At least mine,
that sleeps all day.
I would say that hip (or hepp as they say in the Northeast jazz scene) refers only to ability, whereas "cool" refers to personality and personal charecteristics. A fun, easy-going person is referred to as "cool", while a person who possesses some sort of new, exciting ability (again, as in the case of 1950's bebop muscians) is called "hip".
Commenting by HaloScan
