Your writer - a bespectacled, earnest, and let's face it pretentious 35 year-old who tries too hard to go for lo-fi indie nerd chic - really isn't best positioned to determine that which is and is not cool.
But there are certain pro wrestlers who simply are and are not. It's a disposition thing, and it's all linked, inextricably, to effort. That punctuation and the friggin' word "inextricably" supports that first point. Jon Moxley is very cool, and he would never use the word "inextricably". He doesn't use Twitter - an awful hell-scape of a digital second life in which waves upon waves of uncool people call one another lame - because he doesn't need the validation or the petty, exhausting drama.
He rolls out of bed, drinks straight liquor, beats the sh*t out of people after advising them of the specific way in which they are to endure painful head trauma, drinks more straight liquor, and drives his van back to his remote home with Metallica blaring in the speakers. He still has the same CD he burned from the library. He wears leather and gets away with it. He is piss funny and he does not give a f*ck. He could also get away with riding a hog. But he doesn't. That is the key difference.
These people are not Jon Moxley...
10. Stephanie McMahon Wears A Kangol Hat
Yes, maybe Stephanie McMahon knew what she was doing in 2001.
Maybe a shred of self-awareness drove her to wear a leather Kangol hat emblazoned with the ECW logo. Maybe the idea was that you were meant to receive her as an overbearing corporate pretender to the underground throne. Maybe the hat itself put the horrific juxtaposition over the top.
But if WWE truly was self-aware, they'd have actually cared about what its audience thought about the Invasion angle in the first place. They might have realised that there was more money - and less audience-haemorrhaging nihilism - in positioning ECW and WCW as threats. If Steph herself had an ounce of this human quality, she wouldn't have compared the 9/11 terror attacks to her father's indictment.
The leather Kangol hat, therefore, was not heat. It was something Stephanie McMahon wore to look cool, perhaps after first learning of the existence of MTV2. It looked like she thought she was hot sh*t, palling about with the gang.
Her aesthetic was so painfully try-hard for what was kewl at the time that it's a miracle she didn't tell you f*ckers to get up and get down with the sickness.