When: 2009-present

Terry Richardson's work with Supreme is ongoing and has produced some of the brand's most notable pieces. He's photographed Kermit the Frog, Three 6 Mafia, Kate Moss, and Lou Reed for T-shirts or editorials and has helped open Supreme up to a larger audience. Depending on how you look at things, this is either the best or worst thing that's happened to Supreme, but Richardson's gritty style of photography is the street culture edge that works for the brand and each collaboration—no matter the topic—has been successful.