25. Nike SB Dunk Low "Entourage"
Year Released: 2011
Entourage was the quintessential TV show for the slacker-turned-famous-friend-of-a-film-star wannabes that would rather skate than go to work (takes one to know one, right?). When Nike SB decided to add a gum bottom to the all black upper with subtle Elephant print, the combination is damn near perfect to wear every day. Not many shoes you can really see yourself wearing with anything, to do anything, but the Entourage Dunks are one of them.