My Own Private Idaho (1991)
Man, shit gets real in this film. Keanu's turn as a street hustler opposite other 90's icon River Phoenix is part Fear and Loathing in Las Vegas with a dash of Easy Rider and some Reqiuem for A Dream on the side. Gus Van Sant's film, loosely based on Shakespeare, outfits Keanu in a badass motorcycle jacket and hoodie. His outerwear game is on-point throughout the film, and he also rocks a noteworthy all-over woodblock print shirt.