IMO "cool" is like getting the Sorcerer's Stone ("Philosopher's Stone" in the UK) in Harry Potter. You can never really be cool if you are trying to be cool.

Doing what you want (when possible) and not caring what other people think (i.e. not trying to be cool) is what makes you cool.

People eventually see through those who are just trying to act cool, but are not being cool. AKA "Posers" who don't get the Sorcerer's Stone of coolness.

This usually means that at the time there will be plenty of people who say you are weird, or a loner, and/or a loser. Then years later someone will say, "Oh, I remember you. You were that cool person doing your thing while everyone else went with the crowd."