I don't think you understand what the word cool means.... Being cool is about not participating in traditionally enjoyable experiences and creating the illusion that happiness can be found in alternative, less enjoyable experiences. The degree to which other people around you try to emulate your alternative lifestyle and fail determines how cool you are. You're only as cool as people wish they were.

True cool is an attitude that is projected from a person who is extremely comfortable in their own skin. Cool people have the ability to forge their own paths, stand apart from the herd, and not give a damn about fitting in. A person who is truly cool is a work of art. And remember, original works of art cost exponentially higher than imitations. Just take a look at the the coolest people in history. They will always be a part of history for being extremely original individuals, not imitations.

Sounds cool. Looks cool. Feels cool.

What you don't want is a product to be cool. You want it to be a part of people's everyday life.

I'm up to here with cool, okay? I am so amazingly cool you could keep a side of meat in me for a month. I am so hip I have difficulty seeing over my pelvis.

The essence of cool, after all, is not giving a fuck. And let’s face it: I most definitely give a fuck now. I give a huge fuck. The hugest. Everything else — everything — pales. To pretend otherwise, by word or deed, would be a monstrous lie. There will be no more Dead Boys T-shirts. Whom would I be kidding? Their charmingly nihilistic worldview in no way mirrors my own. If Stiv Bators were still alive and put his filthy hands anywhere near my baby, I’d snap his neck — then thoroughly cleanse the area with baby wipes. There is no hope of hipness. As my friend A. A. Gill points out, after your daughter reaches a certain age — like five — the most excruciating and embarrassing thing she could possibly imagine is seeing her dad in any way threatening to rock. Your record collection may indeed be cooler than your daughter’s will ever be, but this is a meaningless distinction now. She doesn’t care. And nobody else will. If you’re lucky, long after you’re gone, a grandchild will rediscover your old copy of Fun House. But it will be way too late for you to bask in the glory of past coolness. There is nothing cool about “used to be cool.” All of this, I think, is only right and appropriate.

Maybe you are the “cool” generation … If coolness means a capacity to stay calm and use your head in the service of ends passionately believed in, then it has my admiration.

If only I could be as cool as you

I'm still alive, which is pretty cool.

It's not cool ... or it's not cool enough. The world is getting warmer, that's all there is to it. I want you guys to stop this. I want you to change the world.

Not cool. Ever. I’ve never been cool and I don’t really care about being cool. It’s just an awful lot of time and hair gel wasted. At school I was a medium-clever geek. If you’re at public school (Sherbourne) and you’re not that good at rugby, you spend quite a few important years of your life feeling like a real loser. We’ve never been about cool. What’s happened to us is more about showing that the geeks at school can get there in the end. And you have to stay true to who you are, the root of all this is to do with our friendship. source

On smack, I was cool and confident, so collaborating was easy.

Makeup is cool. I mean, you can turn up and feel really good and treat yourself, but it shouldn't be something you hang on to to validate your beauty or something you have to do to make you feel beautiful.

There is nothing cool about “used to be cool.