In the early ’90s, Paul Thomas Anderson left New York University after two days in film school. Shortly thereafter, he made Cigarettes & Coffee, a short film he funded using gambling winnings, charges made to Anderson’s then-girlfriend’s credit card, and $10,000 his father had put into a college fund. (Interestingly, the plot follows a $20 bill.) The film was accepted into the Sundance Film Festival’s Shorts Program, and plans to make it into a feature-length film were greenlit the following year.
Since then, the Los Angeles-bred director has released nine feature-length films, received eleven Academy Award nominations, and collaborated with some of the most recognizable names in Hollywood, including Adam Sandler, Julianne Moore, and Daniel Day Lewis. He has the relaxed and confident air of a guy writing the cult leader (The Master), porn prodigy (Boogie Nights), and stoner anti-hero (Inherent Vice) protagonists he’s always wanted to write.
Style-wise, Anderson stepped onto the scene in the late ’90s wearing Adidas slides and a slightly sleazy, in-your-face look befitting of a precocious emerging director. (His girlfriend at the time, it’s worth noting, was the ultimate indie sweetheart Fiona Apple.) As his career flourished, Anderson’s wardrobe shifted away from the gonzo vibes of his youth toward a more practical and toned-down uniform. Think: French director, sans the inconvenienced demeanor. Rumpled button-ups tucked into straight-leg jeans, paired with a leather belt and mountaineer-style shoes. He’s also been known to don a schoolboyish peacoat here and there.
Anderson’s hair has had its own parallel journey, although a less linear one. The director’s grooming has oscillated from clean-shaven with a floppy self-cut shag, to bed-headed and rocking what one of my coworkers called a “Civil War beard,” and back again. (With PTA, the pattern seems to be: the crazier the hair, the more esoteric the film.) Recently, Anderson revealed an all-white beard while promoting his latest film, One Battle After Another, which lands in theaters today. Given the wackiness of those whiskers, I’m betting it’s going to be a good one.
In honor of Anderson’s tenth movie, we’re taking a look back at his best fits. You’ll find that his best accessory—that signature puckish mien—has remained intact since his first chaotically produced short.