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

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