With personalities that are as big as their bank accounts, rappers usually have the cavalier attitude required to don some of the most outrageous clothing that most of us normal people can't even fathom attempting. That being said, the fedora is officially the worst hat ever, and so fashion's most daring may have met their match.

Can the bravado and swagger of hip-hop's finest make fedoras work? The overwhelming answer is no, but it's fun to watch them try—just click through to judge for yourself. From old school originators to today's chart-toppers, here is a gallery of Rappers Wearing Fedoras.

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