8. Varsity Jackets

Given hip-hop's long affair with sports, it's a no-brainer that rappers like J. Cole and Wale would rock varsity jackets on the regular. Once we started seeing interpretations from designers like Balenciaga on the backs of celebs like Chris Brown, it was the beginning of a trend. Kid Cudi was often spotted wearing GANT Rugger's Homerun jacket, and Drake even made his own version for his October's Very Own clothing line.