The Wins And Fails Of Hip-Hop Clothing Deals - Page 3
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Source: Paul Warner / Getty
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Take a look below at 8 figures in the hip-hop world that went from music to fashion with varying results:
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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

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

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

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

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.
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