Back in 1995, Supreme crew members slapped a Supreme box logo sticker onto a Calvin Klein ad featuring the lovely Kate Moss. The squad was paying homage to the ad and placing their sticker on it as a form of respect. Calvin Klein didn't see it this way, and the company filed a lawsuit. Almost 10 years later, Supreme turned that whole situation on its head by releasing the ad, with the sticker, on a T-shirt, perfectly embodying the witty "zero fucks given" attitude that lies at the center of streetwear's collective mentality.
Honorable Mentions: Andrei Molodkin "Fuck Bush" Skate Deck, Martha Cooper L/S Photo Series Shirt, Vans Skate Hi SL