Dimitrios Kambouris/Getty Images
Lindzi Scharf
July 09, 2013 AT 07:32 PM EDT

Name checking a designer in a song is nothing new in the world of music, but Jay-Z takes fashion-related rap to a new level on Magna Carta Holy Grail.

“Tom Ford” is an ode to one of Jay’s favorite designers. “I don’t pop Molly, I rock Tom Ford,” he raps, declaring that Ford’s clothes are his drug of choice. In an interview with Billboard, Ford said he’s “completely flattered” to have a song named after him.

But before he rocked Tom Ford suits and ties, Jay’s go-to ensembles included streetwear from his own Rocawear clothing line, ill-fitting suits, and outfits that appeared to be carefully coordinated to match those of then-girlfriend Beyoncé. Click on to see some of Jay-Z’s biggest fashion hits and misses. 

That’s do gangster! At the 1999 MTV Movie Awards, the “Big Pimpin'” rapper accessorized his suit and tie with a do-rag, a look he later described as “corporate thuggin.’”

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