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When hip-hop entertainers make it to a certain point in their career, the obvious next step is to think big by stepping outside of music and developing business in other areas. One of the first routes many go is into the fashion industry, especially given how much style has impacted the genre over time.

Mercedes-Benz Fashion Week Spring 2009 - Sean John 10 Year Anniversary

Source: Paul Warner / Getty

Kanye West — a genius to some, egomaniac to others —  is one of the most successful artists to make a leap into fashion by collaborating with a who’s-who of today’s top labels — Nike, adidas, A.P.C. and Louis Vuitton are just some of his big-name partnerships.

His latest collaborative effort is with everyday-wear fashion giant Gap, which has been going well under its YEEZY GAP imprint up until recently.



Ye is currently on one of his soon-to-be-deleted Instagram rants at the moment, where he’s continuing to call out Gap for doing business dealing behind his back amongst other shady moves. “Gap held a meeting about me without me?” the GRAMMY-winning rapper recently posted to his over 16 million followers (seen above), accompanied by a photo that appears to be in a showroom with the controversial new YEEZY GAP Engineered By Balenciaga collection laid out on the floor.

RELATED: A Black Entrepreneur Says Balenciaga Used His Design Without His Permission

Currently, he’s posting a string of IG posts that started with a video of him laying down to Gap execs in Atlanta a passionate argument for ownership and creative freedom. The clip ends with him even threatening to quit if it doesn’t happen. Other videos appear to be what looks like Kanye assembling to go independent, captioning one post by writing, “The monster(‘s) about to come alive again.”


While we can’t confirm how long any of those IG post will stay up on Kanye’s page, we wish him nothing but the best on his quest to build a global fashion empire on his own terms. It got us thinking about a few other entertainers that had similar aspirations, and how many won versus the few who found themselves in the same “Gap trap” that Ye is currently in.

Take a look below at 8 figures in the hip-hop world that went from music to fashion with varying results:




1. WIN: Diddy, Sean John

Beyond the undeniable success of Sean John in the late ’90s and throughout the 2000s, the biggest win of Diddy’s namesake label is that he recently bought it back and plans to do a relaunch to cash in on the current Y2K revival.

2. FAIL: Nelly, VOKĀL

Nelly - MTV Video Music Awards 2003 Source:Getty

Although its sister brand, Apple Bottom Jeans, saw more success for Nelly back in the 2000s, VOKĀL unfortunately had little shelf life before it became a discount mainstay at Marshalls. 

3. WIN: Jay-Z, Rocawear

Rocawear is probably the biggest pioneer of the rapper clothing line trope, and outside of Diddy himself was the most successful at its peak. You can still find people rocking it for nostalgia’s sake.

4. FAIL: Eve, Fetish

Macy's Welcomes Hip Hop Diva and Actress Eve To Launch Her New Signature Clothing Line Fetish by Eve Source:Getty

Operating at its peak during the run of her three-season-long titular sitcom on UPN, which she ironically plays a fashion designer on, the line practically disappeared the minute the show went off air. Talk about life imitating art!

5. WIN: Tyler The Creator, GOLF WANG

From successful collaborations with Converse to Lacoste, Tyler is taking the typical T-shirts, hoodies and long-sleeved shirts into a whole new cut-and-sew direction. The results have been amazing so far, and don’t seem to be slowing down anytime soon. 

6. FAIL: Rihanna, FENTY

Robyn Rihanna Fenty And Linda Fargo Celebrate The Launch Of FENTY At Bergdorf Goodman Source:Getty

Although a blip on the radar in her billion-dollar empire, Rihanna’s efforts to do a high-end fashion line under LVMH just didn’t take off with the same success as a much more successful collab at the time with PUMA and her Savage x FENTY lingerie. 

7. WIN: Drake, OVO

As Drake continues to grow in the industry, his OVO imprint follows. The Yorkdale flagship opening illustrated with much cinematic drama above is only one of many shops October’s Very Own has opened in major cities across the globe. 

8. FAIL: Kanye West, Pastelle

2008 American Music Awards - Show Source:Getty

Sadly, Kanye’s current beef with Gap isn’t the first occasion of a fashionable fluke. Many are still salty over his much-anticipated Pastelle line of the late 2000s, easily one of the greatest coulda-shoulda-woulda defunct labels in urban fashion to date.