Get a grip, since this is a site about old bicycles I would imagine most people use criteria like history and heritage to judge whether something is cool or not.
Personally, I use a certain era as criteria for bikes I like and appreciate.
What I don't do is confuse or conflate that era as being necessarily cool. Nobody outside of us enthusiasts would get that - which is precisely, NOT cool.
Surely the concept of us using "cool" is exactly the same as others, like TG, using cool, and it isn't necessarily just what a group of enthusiasts would thing of as cool - which is why cars like the M3 and the M5 are uncool.
As for what history and heritage are who on Earth are you to define what it is in this or any other context?
Just as important as any other take on the subject, that's what.
'cept I'm not confusing "cool" with "what I like".
Or should I bin my OED and replace it with a NED.
Whatever lights your candle