Tom Wolfe Defines 'Cool':

According to Tom Wolfe, 'cool' = manly.  Only men can be cool to start off with, which, when thinking back, is true.  Girls are cute, guys are cool, it's just code for feminine/masculine.

What traits do cool people have?  It's sort of interesting, because it isn't pure socioeconomic status, which means people of all sorts can angle in on this treasured adjective.

Again, going by Tom Wolfe's definition:

Cool people are confident.  They're fearless, don't take offense to anything, are never defensive about themselves, and just glide through life unperturbed.

Perhaps for this same reason, cool people are never enthusiastic or passionate about anything, they want for nothing, so they can't be shown to be overly desirous of anything.  A desire is a weakness, it means you would demean yourself in exchange for it.  Cool people never have to stoop or scurry for anyone, and the way they do that is by betraying no desire for anything anyone else has to offer.

A cool person never has to exert himself to get what he wants, it just comes effortlessly and naturally into his lap.

If people try to intimidate you physically you just give them a quizzical look, like, what planet of the apes are you from?  If they try to demean your looks, intellect, honor, family, or reputation, the only proper reply is a disdainful disinterest.  The yapping dog is so far beneath your notice that nothing he/she says is even communicated to your lofty ears.

Cool men are never in heat around girls, they can take their time and make their move whenever they want, because it really doesn't matter much to them whether you give in or not.  Cool men are happy to break off an encounter without pressing for more time together -- they know the girl will always come back to them wanting more themselves.

Now, this may be very cool, very manly, and very attractive to women.  Unfortunately, it's also very inhuman.  It means you can never love a woman, which does in fact evince passionate attachment and vulnerability to their disapproval.  It means you can never enjoy a hobby, because it betrays an overly 'childish' obsession with some dorky pastime girls don't care about.  It means you can never set the record straight when people insult you, because that looks 'weak' and 'defensive.'  There's a reason normal people aren't cool, because it goes against all your immediate instincts and desires and always counsels the exact opposite.

Also, if you never exert yourself, you're likely to fall behind the efforts and ambitions of those who will, and then your socioeconomic status will drop.  You can make up for that around women with your cool aura of attractiveness, but wealth and power are useful in their own right, not just to impress women, and now you have less of it than you could have had.  Ideally a cool person would exert himself very much, just never in the presence of the people he's trying to impress, where the fiction that everything comes easy to him can be maintained, but now you have to live a lie with the people who matter most to you, who don't actually love you, but just some pleasant fictional character you've created, so to what avail?

I'm sure being cool is good advice to attract ladies.  I can't think of any instance where a cool guy didn't get the girls better than the un-cool guy.  But I don't think the tradeoffs are worth it.  You're better off being yourself, never being cool, never attracting the ladies, but at least getting to truly love the things you love and be truly loved by the people who truly love you.  It's worth a lot more than anything coolness can buy.