Ranking What Was Really The Best Wrestling Attire Every Year 1990-2021

23. 1999 - The Rock

Bret Hart Young Bucks
WWE.com

If "cool" is measured by an ability to pull off the absolutely ridiculous, the Rock was the coolest man on the planet in 1999. He wins Best Dressed for a year in which he wrestled in a value range knockoff tracksuit for three months. That's how cool he was.

He looked cool in the ring after that, without much trying: the regulation black trunks and boots suited him well because he never lost sight of when business had to be done. He was never a joke.

When he trash-talked his utterly beleaguered opponents - it's a good job Triple H wrestled like Triple H in 2000, because Rock made him look like Billy Gunn in '99 - he did so wearing the most garish unbuttoned shirts because he could. You couldn't. You might have wanted to, in your most optimistic moments. If you could get away with it, you'd walk out of lockdown and into a pub with your pecs out right now. But you can't.

You are not The Rock.

 
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Michael Sidgwick is an editor, writer and podcaster for WhatCulture Wrestling. With over seven years of experience in wrestling analysis, Michael was published in the influential institution that was Power Slam magazine, and specialises in providing insights into All Elite Wrestling - so much so that he wrote a book about the subject. You can order Becoming All Elite: The Rise Of AEW on Amazon. Possessing a deep knowledge also of WWE, WCW, ECW and New Japan Pro Wrestling, Michael’s work has been publicly praised by former AEW World Champions Kenny Omega and MJF, and current Undisputed WWE Champion Cody Rhodes. When he isn’t putting your finger on why things are the way they are in the endlessly fascinating world of professional wrestling, Michael wraps his own around a hand grinder to explore the world of specialty coffee. Follow Michael on X (formerly known as Twitter) @MSidgwick for more!