you’re right, it is the work of your 20s (and 30s…..and 40s….) to figure out what “cool” means and how to embody that for yourself. you’re right on schedule!
I highly recommend taking the search offline almost entirely + not forcing it. think about the coolest people you actually know in person. what traits of theirs classify them this way? the more you start looking for traits you admire in the people around you, the more you’ll find yourself weaving your version of that into your life. we’re all tapestries of the people that have made us.
also, you write: “i often feel far more fixated on appearing “correctly” than most” -- feelings are not facts and I can assure you that everyone else is also just as internally focused. start looking for the ways you ARE connected and similar or even the exact same as the people around you — social cohesion is the key to being cool, and there are always more similarities to be found.