Ever since the twin releases of Bottle Rocket and Hard Eight in 1996, gen-X filmmakers Wes, and Paul Thomas Anderson have made a name for themselves with richly textured films crammed full of memorable production design, and lush costuming.
While there’s no end to the amount of iconic outfits in the Fashionable Andersons’ oeuvre, in this blog series we’ll look at each director’s own wardrobes, and trace the evolution of their respective fashion styles in the last 30 years beginning with the 1990s. Each in their 20s by this decade, both Fashionable Andersons embody a youthful, carefree attitude in their fashion choices during this period.
Paul, a California casual king, keeps comfort at the highest priority during this period.
Wes, meanwhile, was born and raised in Texas, attending a private academy that enforced a dress code. A history that extends into dress as well.
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1990 
Pictured here around ‘89-’90, is one of the earliest pictures of Wes posed next to his classmate and future collaborator, Owen Wilson.
Both men’s hair is cropped short around the sides and back, but spiked straight up on top. Even though Wilson is in a short sleeve t-shirt, Wes wears a long sleeve polo PLUS a turtleneck underneath. Meaning that Wes gets cold very easily, or is immune to heat.
Beyond that however, there isn’t much to remark on. No jewelry, no accessories (except a belt). It’s a pretty simple, collegiate look for any occasion.
1992
When he was twenty-two, Paul Thomas Anderson was a PA for a CBS television movie called Secret Vows (later retitled Sworn To Vengeance). The above video filmed during production of the movie, shows Paul in this period, at a primordial phase of his fashion development (and already on the road to his coffee addiction). A rosetta stone from which all things descend.
Dressed like some hypebeast from 2019, Paul is layered up for what looks like a very cold, late November autumn. In the latter part of the video when Paul speaks to the hair and makeup department, he facetiously jokes about needing a trim, but his hair is still quite stylish. With the early nineties camera quality the colors are difficult to make out, but Paul seems to be wearing an olive sweatshirt underneath a similarly toned grey or olive shell bomber jacket. A small bit of his white shirt sticks out at the top. A great look then as it is now.
The angles of the video only ever show Paul’s top half, so the pants and shoes he’s matched with the outfit are never seen. However, the accessories he has on are paramount. The sunglasses have a burgundy tint (a la Jack Horner), but are decidedly NOT aviators. Still, the wide frames are complementary and evocative of the 70s in line with the 90s fashion trends.
Also of note, is the MAN RING on Paul’s right ring finger. It’s a simple, silver band from a trend that seems all but gone in today’s modern fashion culture. Even out of the half a dozen or so other men that Paul encounters in the video, he is still the only one seen wearing a ring for fashion.
1993 
Pictured here at the Sundance Lab, Paul Thomas Anderson directs the crew of his short film Cigarettes & Coffee. Clothing wise, he looks to be wearing denim jeans, a dark linen shirt layered with a white t-shirt underneath. Notable accessories include a trucker hat stuffed in his back pocket, a black casio watch, and his silver ring makes another appearance as well.
Paul is also wearing circular frame eyeglasses, giving the impression that his sunglasses in the production video may have been prescription?
1994 
The next January, Wes Anderson and Owen Wilson found themselves at the Sundance film festival as well, premiering the black and white short that would be the basis for Bottle Rocket.
The Utah winter prompts both Wilson and Wes to finally get on the same page about how to dress for the weather. In addition to a backpack, Wes is bundled in a turtleneck, scarf, fleece sweater, and wool coat. There is also a large white button on the front of his coat that is unreadable, but perhaps Sundance related.
Speaking of cold weather . . .
1995 
Finally on the set of his first feature length film, Paul directs his star Phillip Baker Hall in an exterior scene for Hard Eight. Given the Nevada weather, our California boy is bundled up in a large black parka, black scarf, leather mittens, and a beanie. He’s got the same wireframe eyewear seen from the set of his short film Cigarettes & Coffee, and headphones wrapped around his neck – director sheik.
Another set photo from Hard Eight. Paul sits in a classic director chair in between scenes. The weather isn’t as cold this time around, allowing him to wear a single layer: a short sleeve cotton shirt. He appears to be wearing the same watch as he did on the set of Cigarettes & Coffee (1993).
This time around, no specs.
Wes Anderson, with his hair perfectly coiffed and messy, catches the lens of the camera while on set of the feature film production of Bottle Rocket. He’s got on a large winter parka with faux fur fabric around the collar, and wrapped in a scarf.
New additions this time around are his eye glasses. Not quite rimless like Paul’s, but still clear see-through frames. Minimal and timeless.
The clear eyewear makes another appearance on set of the feature film production of Bottle Rocket. Owen Wilson takes direction while dressed as his character Dignan in a terribly retro shirt.
Wes meanwhile, wears a red fleece that gives him an uncanny resemblance to his character Anthony Adams (played by Luke Wilson in the film).
Another day on the set of Bottle Rocket. The interior shoot means Wes can lose the fleece sweater, and keep it simple with a purple plaid flannel shirt. The clear framed glasses make a return.
In a (perhaps staged) production photo for Bottle Rocket, Wes edits the film with co-leads and co-Wilsons, brothers Luke and Owen, in tow. Wes’ hair is more vertical than in the previous set photos. He layers a white collared shirt with a baggy cardigan.
1996
Paul on set of his second film – an elaboration of a short he made in high school – entitled Boogie Nights. Next to him is the legendary actor Burt Reynolds, himself playing a film director from 1977.
Shot in the summer, Paul sports a buzzed haircut, and blue short sleeve linen shirt that’s both stylish and breathable. As far as eyewear, Paul is sporting some orange tinted sunglasses with some oval shaped frames seen elsewhere in production photos.
Another day on the set of Boogie Nights, same orange glasses as before. This time around, Paul is wearing an even more breathable, green shirt. Perfect pool fit.
From this angle it’s clear that these are not the same sunglasses from the 1992 video.
1997
Pictured here in London for the release of Hard Eight in March of ‘97, Paul’s hair has grown since production on Boogie Nights wrapped a few months earlier. For the picture, he’s wearing his oval eyeglasses from before, but ditches a coat and tie, opting instead for a simple striped blue shirt and matching pants. For the first time, we see some footwear! Black dress shoes, and beige dress socks.
Variations on this look would persist until the release of Boogie Nights in October of the same year.
Paul interviewed on TV for the release of Boogie Nights in October ‘97.
Now in production for his second film, Rushmore, Wes returns to his prep school fashion roots. Untucked collared shirts, pleated trousers, no ties. He continues to wear the same glasses as he did on the set of Bottle Rocket.
In this color photo from the same baseball scene, we see the colors that Wes chose for his outfit. Brown Corduroy pants, light purple shirt, and navy undershirt.
On this day, Wes goes with the white on white shirt combo. Jason Schwartzman makes sure he’s cleared for landing.
1998
Paul Thomas Anderson and Fiona Apple attend the 50th Annual Writers Guild Awards, where Boogie Nights was nominated for Best Original screenplay.
Paul has a plain black suit, blue tie, but the real stunner here is Apple, showing her support with a white Boogie Nights t-shirt.
The award would end up going to Mark Andrus and James L. Brooks for As Good As It Gets.
Boogie Nights was later nominated for Best Original Screenplay at the Oscars – Paul’s very first recognition from the Academy! He keeps his look low-key and classic with a simple black tuxedo.
The Oscar would go on to be awarded to Matt Damon and Ben Affleck for Good Will Hunting.
For Paul’s third film, Magnolia, a video production diary was made and included on the DVD. It documents the film’s complete development, from pre-production to first premiere, and shows first hand the director’s fashion choices in the final days of the 20th century.
For this film in particular, Paul tends to wear suits or sport coats during the production more than in any other. As he gives an inspirational speech on set before the first shot of the movie, Paul wears a black suit, white shirt, and no tie.
He substitutes his jacket with different sport coats throughout the film.
1999
With Rushmore a certified success, Wes makes his debut TV appearance on the same program Paul was on the year and half prior. Since it would be televised, Wes dressed up for the occasion.
He forgoes a tie, but dresses it up with a shirt sweatshirt combo in two tones of blue. All topped off with an olive jacket. The glasses make a return as well. Slowly, but surely, turning more and more into the Wes we recognize today.
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That was the 90s for these two directors: a little messy, and a little grunge. But by the end of the decade (and the millennium), both began a metamorphosis of sorts, paying a little more attention to their fashion choices on and off set.
This metamorphosis would continue into the 21st century, as each writer-director was on the verge of making their most mature and impressive works yet.
Stayed tuned for our next blog entry, where we’ll dive deep into the directors’ absolute best Y2K looks of the 2000s.