#11 Sin Cara's first shirt
There was a lot of hype surrounding Sin Cara when he first debuted for the WWE in 2011. The former Místico had made a major name for himself in Mexico, having won Wrestling Observer Newsletter's awards for Wrestler of the Year and Best Box Office Draw in 2006, as well as Best Flying Wrestler in both 2006 and 2007. He was even voted the Best Draw of the Decade (2000-2009), beating out the likes of John Cena, The Rock, and Kenta Kobashi, among others.
Unfortunately, his style didn't mesh well in the WWE. His frequent botching became somewhat of a meme amongst the Internet wrestling community, so it's only apropos that his first shirt was botched as well.
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What was supposed to be just a plain picture of Sin Cara ended up with some strangely-placed shading, creating some overtly-phallic imagery? Embarrassed by this realization, WWE quickly pulled the shirt from circulation, though some still managed to be sold. They're apparently pretty rare, as I couldn't find one for sale anywhere online.
Because of its extremely brief shelf life, this shirt places lower on the list. Still, it certainly belongs here.