Since the days of Adidas tracksuits and gold chains as thick as gym rope, fashion has played an integral part in the culture of hip-hop. 40 years after the advent of the culture, hip-hop has produced its fair share of style icons that have blazed the trails into mainstream fashion quarters. Big names such as Jay Z, Kanye West and André 3000 are known for their impeccable sense of fashion almost as much as they are known for their music.

Of course, nobody is bound to look good every day. Fashion continually moves forward, and sometimes you are going to be left behind wearing something you probably should have left on the rack. Fashion is a serial killer, and it will always claim its victims.

XXL is looking today at some of hip-hop's biggest fashion fails. Here are 20 dapper rappers that look less than fresh.