Max Fischer, Rushmore (1998)
While Rushmore wasn’t Anderson’s first film (that would be the 1995 crime caper Bottle Rocket, which, while enjoying critical success, went largely unseen) it was certainly the project that put him on the map. Part of its charm was the breakout performance given by Jason Schwartzman in the leading role, whose intellectual snobbery as the resident busybody of his posh private school becomes strangely endearing over the course of the film. It’s a transition helped in no small part by the knowingly absurd styling, as Fischer awkwardly models himself after his Parisian avant-garde heroes in ill-fitting berets and papakhas. Bonus points, too, for the first sighting of a hotel porter’s uniform—what would become a recurring Anderson style motif—during a brief, typically surreal subplot in which Fischer disguises himself as a butler to unleash a swarm of bees in the hotel room of his love rival, played by Bill Murray. Because, of course.
Margot Tenenbaum, The Royal Tenenbaums (2001)
Arguably the greatest style icon from any of Anderson’s films, Margot Tenenbaum played by Gwyneth Paltrow had a wardrobe packed with timeless looks that continue to be the envy of any vintage fashion obsessive. Surprisingly, though, most of the iconic outfits were made bespoke for the film—the famous belted mink coat, for example, was a design that costume designer Karen Patch sent to the fourriers at Fendi to craft especially for Paltrow, inspired by a character in an old Peter Sellers film. (Margot’s signature bag, the Hermès Birkin, was a little more on-trend, given she was toting it at the height of the early-’00s It bag craze.) Ironically, though, many of the details most referenced and reinterpreted in the world of fashion were those reflecting Margot’s arrested development as a child prodigy, like her dinky, single red barrette, and slightly too-small tennis dresses. At the same time, all you really need is a kohl-rimmed eye and a severe blonde bob—and maybe a cigarette in the bathtub too, if you’re feeling decadent—to channel a little Margot Tenenbaum.