Born in the wrong era? No. There is no wrong era.

so what is cool?
well, to the rest of the world, cool is relative.
find out what is a subculture. what is "underground". what is "cult".
then, you would probabaly have struck "cool" in it's rawest form.
take the concept, bring it to light, bring it to...the masses.
of course, some people will find such raw 'coolness' repulsive; that's natural, coming from the safe environment that they've been living in.
so you would first have to tone down the rawness and package it in a more... socially accepted way.
now.
people are ready to adopt this coolness and make it their own!
of course, once they do, and it becomes wildly popular,
then...eventually it would become overpopular? overplayed? overrated?
it would become mediocre.
and, it would stop being cool.
time to go back to subcultures then.
however, after people forget about that previous fashion, and move on, it would revert back to its subculture origins again!
hence, regaining it's raw coolness!
so in my opinion, though it's also totally fine to go with what's 'in'
(there IS value in that you know....)
i'd very much just prefer to like what i like simply because i like what i like, there are boundaries to what i ought to like. that is a given.
sometimes you like what others like, sometimes you don't.
i think it's less tiring to like what you like instead of always trying to follow what's cool.
but that's only just my opinion anyway.
cool?