Even though Polo Sport is a diffusion line of Ralph Lauren, it definitely deserves a spot on this list. What began in 1993 quickly became a phenomenon in the streets that was endorsed by Nas, Raekwon, and countless others who rocked the Polo Sport bear and American flag logo with pride. The diffusion line was retired in 1998, but for the years that Polo Sport was around it was a highly coveted brand that, when wearing it, instantly signaled you knew what was up.