When you talk about cool...

There's people who try at cool, people who try and fail, try and succeed...

Cool isn't in and of itself an objective. Even while you appreciate it, you know it's wrong and shallow somehow... those homely average everyday people you normally overlook in your pursuit of it, they get on with their lives and seem to have a kind of strength about them, a vigour that has nothing to do with being "it" or being "in". people who don't have the time of day for that sort of thing because frankly, we should all have better things to do with our time.
I always looked up to those sorts of people, because I've always been one to fold into believing what shop fronts and catalogues told me about the world.

Travel into the inner, south-of-central (or north-east) suburbs where an edge is borrowed from the grit that once shunned the sort of people that now covet lucrative properties there. Forget trendy, their look has earned edge enough not to have to BE trendy. One of this place would know all the good shops, all the night spots.
You can try to be them, with time, practise and substantial but prudent financial investment. But there are others, out there, the effortless, I-never-tried-but-still-got-it kind of dude you pass in the street. With just the right degree of unaffected on-the-spot style and carelessly bad choices. On broken sofas on the porches of side-streets in what must be one of the costliest areas of the city, sipping wine with flatmates on a drizzly tuesday afternoon. Heading out, after nine, huddled in some packed, some KNOWN SPOT corner cafe cradling a house blend double espresso and wearing that morning after like a badge of honour.

He works, he must work, but you never see him at it unless it's somewhere unbearably, self-deprecatingly IT, elusive and exclusive and only ever existing to own its title BEFORE it is ever really known. Not to be known by everyone, that is, by normal people like you and me. To be known by those people who know before everybody knows, who make it their business and art. Otherwise he stalks the street at all hours of the day and night. The streets are his element, the RIGHT. His eyebrow, cuff link, shoelace loosely tied, all figured down to a T. The careful man will have studied the skill; the careless one born of an inate sense for what lies just beyond the sight of magazines and street fashion blogs.
He cruises, seen in the kind of locales that will intrinsically complement his style and exhibit his good judgment, knowing there's nothing he could possibly add to what he's got on show right now.
He sees others. He reads what they've written in their vintage threads to him, in their shaved heads and layered, torn stockings. There's no envy at that level, only admiration, because every true artisan appreciates another's craft.

Somewhere a long way away, at another time and place he might smile at old ladies, be called Gary or James or Peter, but that all doesn't matter. The personality, the life in the context of the man in his element, at that moment that your eyes meet him and his impeccable chauffeur cap, is irrelevant.
He is the moment, there for the moment it takes you to see and process him, gone the next. Burnt into your retinas as the flawless image of something intangible but there, unspeakable but present, like an animal smell. It speaks to the hindbrain.
It says things to you, like the most upscale and cutting-edge rags say things to you without words, without hard-sell or viral campaigns. It's an image, a feel, a concept. And he owns and embodies it... strangers are his friends, because for that one shallow moment in which a stranger accurately assesses to intricate detail everything about him, he will see the man and take away an immortal, impeccable, flawless impression in his mind of everything the man has perfected.

He is a concept on legs. You don't need to perceive him as anything else other than the stranger on the street, because he is the perfection of that stranger.
He is cool. He owns cool. He is part of the ever-changing dialogue that hides away from strangers and exhibits just enough to earn the love it needs in its constant pursuit for freshness, aesthetics, style, meaning, visuals.

He is the man on the street.