If you have to ask about it, or have to think about how to be cool, you're not.
(this is the general "you", meaning you, he, she, they, them, me, us... not you-you)
If you take exception to being called uncool, you're uncool... simply because you think you're cool. Cool people don't think they're cool. They don't care.
It's like
The Game. I've just lost "The Game" (but managed to keep at it for months, this time...
) because I've thought about it. You've just lost it because you read it.
"Cool" isn't something you set out to be. Which means a Ferrari is never cool, because people buy Ferraris to be cool. It's only cool when it's not a particularly good Ferrari for being cool in (the Ferrari F40 is a good case in point... because it's an awful road car... the F50 because it's awfully ugly...
).
An old Porsche 911 is cool. A new one isn't, because people buy them specifically to be cool, which is not cool.
An old Mini Cooper... well... the nice thing about old Mini Coopers is that
cool people actually buy them simply because they like them... which makes them cool.
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And yes, I'm notoriously boring and uncool when talking about cars. I'm somewhat cooler (according to people I know) when I'm not. But to not talk about cars just because I don't want to be uncool is seriously uncool, which is why I don't really heed their advice to shut up and am content to be as uncool as I want to be.