Be Smart! Be Brilliant!
Whenever you find yourself on that long, low road to "cool", just remember... if you have to search for cool, you'll never find it. If it's not already inside you, you can never find it outside of you, unless someone else has it. You can get close to cool, but you can never absorb it.
Wikipedia defines "cool" as: Something regarded as cool is an admired aesthetic of attitude, behavior, comportment, appearance and style, influenced by and a product of the Zeitgeist.
You are either meant to have it, or not. You can build towards having it, but it has to come naturally. And so the only way you can really get it, is to just have it, as it comes from within; you can't force it. Just be yourself.
Now that... is being cool.