23. Arrested Development
Arrested Development's conscious rap predates the backpack look and their Afrocentric style is a great example of the cyclical nature of trends. At the time, gangsta rap was at its peak and style trends followed suit. What earns Arrested Development a spot on this list is that when we look back now, there are a few pieces Speech and his crew rocked that would look cool today, even if at the time it was long on its way out.