7. Lupe Fiasco
Lupe Fiasco used to be the most stylish rapper in the game, had his own blog on Hypebeast, and started a cool streetwear brand, Trilly & Truly. But those days seem like an unrecognizable memory compared to the rapper's present-day style.
He has recently modeled lookbooks for U.S. Alteration, but there's something off about Lupe's personal style. He didn't even make our latest ranking of Chicago's Most Stylish Rappers. Last year's altercation with Chief Keef left the once-thoughtful emcee void of his confidence—and it has spread to the way he dresses. He doesn't own any of his looks. It's sad to any hip-hop fan he assured, "you want the realness? Hey, I gotcha."
We're waiting, Lupe. Grab some new threads. Hip-hop and the style world miss you.