10 Embarrassing Times Wrestlers Tried To Look Cool

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.