6. OG Kate Moss Tee, 2004

I suspect a lot of people who grabbed the 2012 Supreme Kate Moss Tee don't know the story behind Kate Moss and Supreme. In 1994, Calvin Klein ran an advertisement campaign featuring the young model. Supreme had just opened, and slowly but surely the brands logo began to appear around the city in the form of box logo stickers. It just happened to be that a favorite location for these stickers were over those very prominent Kate Moss ads. Calvin Klein got their panties in a bunch and sued Supreme. 10 years later in 2004, they got the last laugh by releasing a T-shirt featuring the image of Kate Moss with their logo over her lady bits. This design is truly THE iconic Supreme x Kate Moss because it wasn't really designed at all. Rather, it evolved organically out of the brand's culture and helped the box logo become an iconic symbol of rebellion.