21. Staple
If this list were about the Top 50 streetwear designers, Jeff Staple would dominate. Splitting his time and direction between retail (Reed Space), his magazine (Reed Pages), and his design agency, his own streetwear brand Staple is more a platform to flex his muscle. Complete with intelligent T-shirts, progressive technical jackets, and fashion-forward street-minded pieces, think of the Staple brand as a really fancy business card for his design prowess.