They don't have the slightest idea WTF cool is. It isn't donning a pair of sunglasses and playing the sax. It isn't wearing a certain style of clothes or using hip language or going to a basketball game. That's all nothing but a bunch of superficial image shit meant to impress the immature and intellectually stunted such as one finds at DU.
Cool comes from the inside. It's manifested by facing adversity yet struggling onward with a positive attitude. It's about being able to keep your emotions in check and reason things through while everyone else is panicking. It's about being kind to the weaker when you don't have to be and being tough when you need to be. It's about intelligence and great courage coupled with humility. Those are not things you can wear or promote or advertise, and they reside within people whom you'd never know had them unless you spent some actual time with them on a personal level.
When you're cool, you don't give a shit who thinks you are or not. In fact, the thought doesn't even cross your mind. It's just reflected in your character and natural demeanor. Some of the coolest people I've ever met are combat veterans, who've experienced Hell, yet pushed on to lead quiet, unassuming lives, taking care of their loved ones and showing compassion and understanding to their fellow man depite having been thrust into horrific situations the uninitiated can't even imagine. Some of the coolest people I've ever met also include those who've faced austere or tragic beginnings, and drew on their inner strength to accomplish things, to work to their potential to be the best they can be, without blaming others for their hard times or feeling entitled to something not theirs.
That's why I see very little "coolness" on the Left today, because their icons pretty much represent the polar opposite of that described above. Their "courage" is a strident voice in a bullhorn amongst the mob and their "compassion" extends no further than that which can be extracted from their neighbours' pockets at the point of a government gun. All the Che t-shirts and musical insruments and fancy rhetoric on the planet isn't going to make that "cool".