
My brother is a writer and an editor. He has worked for many big deal magazines. Once years ago when he was a young kid he had a assignment for one of the "Lad" magazines. To write about cool. So he asked me what I thought.
Now I think you are either cool or you are not. If you have to think about it you definitely are not. If you have to strike a pose no way.
Steve McQueen is cool, Tom Cruise not so much.
You can't recapture your youth if you thought you were cool back in the day. Because you see people laugh at that. Just as much as they laugh at somebody who is old trying to be young. A sixty year old broad with a tramp stamp or a piercing. A fiftyish guy with a sports car and a fancy hair cut. You can be cool if you are old. Just be honest and do cool shit. Then people will want to do what you are doing because it is cool. Not because you are a poser.
Derek Jeter cool, A-Rod not so much.
Most of all to be cool, be true to yourself. Have your own style and not give a shit what other people think. Don't try to force them to agree to what you think or how you act. If it is cool don't worry people will laugh and enjoy it or even follow along and get the joke.
Titus cool, Jeremy/Michael/Luckyoldson not so much.
So be cool.