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

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.’”

In 2000, Hova turned the Hollywood premiere of Nutty Professor II: The Klumps into his own personal white party.

Jay brought a some street style to New York City’s Metropolitan Opera House when he performed wearing a Chicago Bulls jersey and a pair of Air Jordans at the 2001 MTV Video Music Awards.

In 2002, Jay and Beyoncé showed Britney and Justin how to do denim outfits right when they stopped by MTV’s TRL to perform “’03 Bonnie & Clyde,” their first collaboration together.

The rapper looked dapper at the 2004 CFDA Fashion Awards in New York City.

Jay and Beyoncé dressed the part when they breezed into Paris for Fashion Week in 2005.

Jay nailed the Riviera nightlife look for Dolce & Gabbana’s “Glamorous” party at the 2007 Cannes Film Festival.

In 2009, Jay kept things casual when he hosted a party celebrating the 10th anniversary of Rocawear, the clothing line he launched with Roc-A-Fella Records co-founder Damon Dash.

Jay and Beyoncé walked his wife down the red carpet — and helped her navigate the stairs — at the 2011 Costume Institute Gala at New York City’s Metropolitan Museum of Art.

They run this town. In 2013, Jay struck a pose with Beyoncé and his Change Clothes collaborator Pharrell Williams at the 10th anniversary party for the Billionaire Boys Club fashion label.