11. Flo Rida
Despite no real support from the hip-hop community, Flo Rida has become a pop sensation. But he still dresses like he has zero credibility within the rap world. The Miami native makes an attempt to get fresh, and swings and misses with one fell swoop. If he's not wearing questionable denim uniforms with protruding spikes, he's trying to get red carpet-fresh, and proving that spending money doesn't make you look cool.
If the rapper could stop trying too hard to be stylish or make fashion statements, he would be better off and find himself removed from the butt-end of Internet jokes. Flo-Rida's biggest issue is he doesn't look comfortable in anything. If he found well-fitting clothes that he actually dug, then perhaps there's hope.