WHEN: Late '90s–present
COMPLEX SAYS: From his "Hawaiian Sophie" days to his button-up shirt movement, Jigga has had a pretty diverse style history. But through all of his looks, his biggest fashion staple has been the Yankees fitted. From the "Do It Again" video to lyrical references in songs like "Empire State of Mind," no other rapper has associated himself with the Yankees more than Jay-Z. Sorry, Joey Crack.

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