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Let’s face it; Jay Z has a winning streak that will most likely never be repeated. He’s got an album library of a legend,  built the Roc-A-Fella empire, wifed the baddest woman in the game, helped bring the Nets to New York and more. While he has a once in a lifetime career, he also has had a fair share of fashion struggles.

With all his fame and fortune we are sure that Jay has access to the finest clothing in the world. It is alleged that A Bathing Ape paid him hundreds of thousands of dollars to wear a purple fatigue hooded sweatshirt for an MTV interview. Heck, he still owns a small stake in Rocawear.

But to many people’s dismay, Hov hasn’t always been able get it right in terms of his style. The result is an often awkward version of Jiggaman who is a far cry from the suave Brooklyn bred hustler we have all grown to admire.

Moguldom Studios recently dropped A Genius Leaves the Hood: The Unauthorized Story of Jay Z, a doc which shows rarely seen sides of one of the most highly accomplished MCs to grace Hip-Hop, be sure to cop the flick that most were afraid to make here.

So we present Jay Z’s top 11 worst fashion moments. Some you know about and other moments will be a definite head scratcher for you. Let us know which get the biggest thumbs down in the comments section.


Photo: Youtube

Sunshine


The “Sunshine” video was the first time the public questioned Jay Z’s cool. The gaudy Versace suits were annoyingly bright and the Hype Williams fish-eye shot gave birth to many years of camel slander that still follows Jay to this day.

Cashmere Jones

Remember Jay’s alter pimp alter ego Cashmere Jones? Thankfully he left the fur and oversized hat behind with that entire ill conceived idea.

Pee Wee Herman

We are not sure what Jay was thinking when he donned this. Matter of fact the gray suit was fine but when he complimented it with a stuffy white shirt that was buttoned to capacity and the tic tac shoes; slander was a certainty.

Chancletas

How could we forget the time when the King of New York was caught wearing open toed sandals with jeans? It is only right to thank Cam’ron for this.

The Faux Skirt

Whether it was a full blown skirt ala Omar Epps, or just double up on a shirt, Hov was looking a little suspect this day at SXSW.

Photo: WENN

Photo: WENN

The Fro

A finely crafted tuxedo went to waste due to an unruly afro.

From Russia With Love

At Barack Obama’s 2009 inauguration Jay went with an oversized Russian fur hat that seemed to overpower his finely tailored suit.

Photo: WENN

Photo: WENN

Skinny Jeans?

Apparently his knots did fit. Marcy Projects shed a tear this day. 

Off Your Shoulder

Remember that brief period where State Property was wearing their shirts off one shoulder. Then Jay got brave enough to do it in the “Girls, Girls, Girls” video? Never forget.

Huh?

Hov wearing capris or nah?

Tennis Time

Thankfully those years of ill used wristbands is past Billionaire Hov. The burgundy was a bit much too, bro.

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