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Wes Anderson Paul Thomas Anderson

The Fashionable Andersons II: The 00s

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This blog is a continuation of our fashion series on directors Wes & Paul Thomas Anderson.

By 1999, much of the world was beset with a collective anxiety over the coming new year. What was seen as destructive in the abstract, was actually cleansing in the world of arts and fashion. An opportunity to reset the cultural router in The Year 2000. Fashion’s Web 2.0 update for the new Millenium.

In retrospect, much of the maligned trends of this era – the baggy silhouettes, the clashing of patterns – seem more quaint and creative than were given credit for. The looseness of the styles, prioritizing a carefreeness in the wake of all that Y2K (and eventual post-9/11) unease that is now sublimating as nostalgia for newer generations.

For directors Wes & Paul Thomas Anderson, the 2000s were a fertile period of creation that produced works tailor-made for indie runways, and ready-to-wear in mainstream multiplexes. The “wunderkinds” from Sundance were now firmly in their thirties, and desperate to out pace their infantile reputations with stronger (and stranger) films than they had ever made before.

This maturity too is reflected in each director’s fashion choices for this period, where both men aspire to be taken a little more seriously and little less boyish.

Grab your hitclips and your pooka shells, it’s the 2000s b—-.



With Magnolia finally out in theaters (and the Y2K apocalypse behind him) Paul returns to TV to promote the film. 

For the interview, Paul’s dressed up a bit more than he did the last time he was on the show. A black suit and tie, hair cut a bit neater, and he loses the glasses altogether in favor of contacts.

Not a bad look to start the millennium. Does this mean we’ll see more formal wear from the promising young auteur?

No more than a few weeks after his TV interview, Paul attends an event for Magnolia at a Borders Bookstore (if you don’t know what that is, ask your parents). 

This look is called: business on top, party on the bottom. Paul goes for broke with a white cotton oxford shirt, red Adidas track pants, and blue suede trainers. As ready for a film Q&A as he is jogging. 

Once again, Paul forgoes his glasses in lieu of contacts, which he will do for the remainder of the decade. A pen is kept in his shirt pocket to satiate any sudden burst of creativity and, perhaps, to sign a few autographs too.

(Original Caption) Tom Cruise and Paul Thomas Anderson (Magnolia). (Photo by Frank Trapper/Corbis via Getty Images)

All of Paul’s interviews and guest appearances would pay off, as Magnolia would wind up with three Academy Award Nominations by Spring of 2000. Pictured here, Paul and actor Tom Cruise attend an Oscars luncheon in Beverly Hills. 

Paul keeps things formal-casual with a red Lacoste polo underneath his charcoal suit (this is just the luncheon after all). His untailored trousers are billowy with a large, open cuff. For footwear, Paul wears a chunky, Steven Madden-like shoe instead of a traditional dress shoe. Old school meets new school.

A few short weeks later, Paul finally attends the 72nd Academy Awards show with Fiona Apple. Magnolia is nominated for Best Original Screenplay, so Paul puts his best foot forward in terms of dress. 

Paul sticks with a timeless, black tuxedo complete with bowtie and cumberbund. His jacket this time around has a much baggier cut compared to the tux he wore at the ‘98 awards show, suggesting a shifting change in contemporary fashion trends on top of Paul’s own evolving taste.

The award for Best Screenplay would ultimately go to Alan Ball for American Beauty.

Emboldened by a rising star profile, Wes attracts multiple A-list actors to be in his next picture, an ensemble piece about family called The Royal Tenenbaums – seen here in the midst of production. In the new millennium Wes continues his aggressively smart-casual approach to dressing on set. 

Here we see, again, his clear-frame glasses, a simple collared shirt, and a chunky, grey sweatshirt tied around his waist. 

This other photo shows the rest of the outfit. This time revealing a black-and-white tartan scarf, grey trousers, and a pair of red New Balance sneakers.

Gene Hackman as Royal Tenenbaum listens along patiently.

Huddled in the trunk of the car for this traveling shot, Wes stays warm with a blue North Face jacket, beige sweater, and corduroy trousers. A camera monitor in his hands, the perfect accessory for any director’s outfit.


Not unlike the protagonist at the center of his fourth film Punch-Drunk Love, Paul also knows the value of a good blue jacket. 

Pictured here (again with a shaved head), Paul’s jacket is worn over a green hoodie, grey pants, and Nike tennis shoes. 

Unlike his protagonist Barry Egan however, Paul avoids wearing suits during the production of this particular film. 

Here, Paul wears a loose short-sleeve shirt with a distinct triangular pattern. Again prioritizing comfort over style, but still achieving both.

Paul in a plain white tee and brown trousers while shooting outside of Barry’s office.

At the grocery store where Barry finds pudding, Paul wears cargo pants (with sides sticking out the pocket) and another polo shirt. Haircut about even with Adam Sandler’s now.


402719 302: Director Wes Anderson attends the 74th Annual Academy Awards at The Kodak Theater March 24, 2002 in Hollywood, CA. (Photo by Vince Bucci/Getty Images)

Wes arrives at the 74th Academy awards in March 2002. The Royal Tenenbaums is nominated for Best Original Screenplay – Wes’ first ever nomination! At the show, Wes begins to resemble the director we recognize today, exercising his right to more ostentatious styling for the event. 

He wears a double-breasted coat with formal lapel in a luxury velour fabric, wrapped in a wool evening scarf, and topped off with an orange paisley bowtie that would make Royal blush. The same white frames he’s always had decorate his face, and his hair is a bit more tame (read: less vertical) than it was in his Bottle Rocket days. 

The award for Best Screenplay would go instead to Julian Fellowes for Gosford Park.

At the Berlin International Film Festival in 2002, Wes poses for his polaroid “Star Portrait”. His film, The Royal Tenenbaums, played alongside Paul Greengrass’ Bloody Sunday, and Hiyao Miazaki’s Spirited Away at the festival.

For the photo, Wes opts for a lighter color scheme. An off white collared shirt under a white shawl collar sweater, underneath a grey blazer. Simple, European, Wes.

To support friend and actor Jason Schwartzman, Wes attends the premiere of a film called Spun (2003). Both him and Schwartzman exude a particular flavor or early 2000s menswear that relied on large patterns, and textured materials.

In keeping with his formal casual predilections, Wes layers a green corduroy suit with a floor length tweed coat (with faux fur collar), a baby blue pullover, gold knit tie, and red gingham shirt. Slowly but surely becoming a more familiar Wes.

At the Cannes Film Festival, Paul stands with his cast for Punch-Drunk Love on the opening day’s press festivities. Given the beach setting, Paul is right at home. He wears his shirt untucked, keeps his hair messy, AND now sports a cool, European beard.

Emily Watson, director Paul Thomas Anderson, Adam Sandler, and Philip Seymour Hoffman at the party at Palm Beach following the screening of “Punch Drunk Love” at the 55th Cannes Film Festival, in Cannes, France, May 19, 2002. Photo by Frank Micelotta/Getty Images

Which isn’t to say Paul can’t clean up when he needs to.

He’s pictured here, in another sharp black tux, with his cast again, this time at the end of the festival before the awards are given out.

Paul Thomas Anderson during Cannes 2002 – Palmares Awards Ceremony – Press Room at Palais des Festivals in Cannes, France. (Photo by Toni Anne Barson Archive/WireImage)

Paul would tie for best director at the festival with Korean filmmaker Im Kwon-taek, for his film, Chi-hwa-seon. 

The award was presented by Cannes Jury President that year, David Lynch.

Mandatory Credit: Photo by Bei/Shutterstock (389903z) Paul Thomas Anderson ‘PUNCH DRUNK LOVE’ FILM PREMIERE, TORONTO FILM FESTIVAL, CANADA – 13 SEP 2002 September 14, 2002: Los Angeles, CA Writer/director Paul Thomas Anderson 2002 Toronto Film Festival – “Punch-Drunk Love” Premiere Photo by Eric Charbonneau ® Berliner Studio/BEImages


By September, Paul would bring Punch-Drunk Love to the Toronto International Film Festival as part of their “Special Presentations” block. 

In a continuation of his dress from the Cannes film festival, Paul wears nothing but a white shirt, beard, and flip-flops in spite of the Canadian weather. A true master of California casual wear, no matter the climate or locale.

Mandatory Credit: Photo by Bei/Shutterstock (389903o) Paul Thomas Anderson ‘PUNCH DRUNK LOVE’ FILM PREMIERE, TORONTO FILM FESTIVAL, CANADA – 13 SEP 2002 September 14, 2002: Los Angeles, CA Writer/director Paul Thomas Anderson 2002 Toronto Film Festival – “Punch-Drunk Love” Premiere Photo by Eric Charbonneau ® Berliner Studio/BEImages


A director’s relationship to their eyesight is the most sacrosanct of all sense relationships. It informs and guides all elements of the film production, from the writing to final color. So it’s important to note that for Wes’ newest film with Bill Murray, The Life Aquatic With Steve Zissou, he ditches his glasses altogether in favor of contacts.

This change in eyewear comes with another fashion evolution for Wes that is unafraid of color and patterns. His hair also changes during this period, growing much longer than before. The result is a messy, voluminous helmet.

Wes in a purple shawl neck sweater with striped trousers and dark Wallabees. 

A result of shooting out at sea, Wes layers up to stay warm. Pictured here, Wes dons a navy peacoat over his purple shawl sweater, white scarf, white tube socks, and tan wallabees.


Tara Subkoff and Wes Anderson, director during “The Life Aquatic with Steve Zissou” New York City Premiere – After Party at Roseland in New York City, New York, United States. (Photo by Dimitrios Kambouris/WireImage)


Tara Subkoff and Wes Anderson during “The Life Aquatic with Steve Zissou” New York City Premiere – Inside Arrivals at Ziegfield Theater in New York City, New York, United States. (Photo by Robin Platzer/FilmMagic)

Wes and partner Tara Subkoff at the premiere of The Life Aquatic With Steve Zissou. 

Wes’ hair is about shoulder length now, meaning he can institute a neater side part that exposes his face more. He dons the same tweed coat from the Spun premiere, on top of a simple white shirt, and blue tie with stars. 


Paul behind the scenes of A Prairie Home Companion with its director Robert Altman. Paul served as an understudy for the film that would take over directing duties in the event of Altman’s sudden passing. The opportunity was invaluable for Paul who had been a lifelong fan of Altman’s work.

In the first photo, Paul wears a long sleeve t-shirt with colored accents along the seams. In the second, he looks bundled in a large black parka. 


Bildnummer: 55089736 Datum: 29.09.2007 Copyright: imago/EntertainmentPictures 2007 – The Darjeeling Limited – Movie Set

Wes on set shooting his newest film, The Darjeeling Limited. Taking a page from his filmmaking inspiration, Satyajit Ray, Wes directs in a white suit, tan scarf, and tan Wallabees. A lighter color scheme that recurs throughout production of the film.

Wes on the tracks. White suit and tan wallabees again.

Paul on set of his latest film, his first adaptation, There Will Be Blood. He directs Daniel Day-Lewis, who ruthlessly portrays the oil driller Daniel Plainview in 1890s California.

In the foggy exterior morning, Paul wears a beige fleece zip-up sweater over a white shirt, olive cargo pants, and brown boots. An outdoorsy palette in contrast to the muddy colored 19th century clothes of Plainview.

On a warmer day of production, Paul sticks with the “old west” theme of the film and wears a chambray denim shirt, tucked into grey pants, with a brown belt. 

Paul also maintains a beard during this period, unlike in earlier film productions where he seemingly shaved on a regular basis.

The same outfit from before, but with a sun hat as well.


Wes and his cast of The Darjeeling Limited. Wes keeps his white suit, but this time he Miami Vices it up with a blue shirt, and no tie. Some pens line his shirt pocket as well.

The film finishes production in time for a September premiere.

At the 64th Venice Film Festival, The Darjeeling Limited makes its world premiere. Wes poses alongside his stars Adrien Brody & Jason Schwartzman for a photocall.

Wes continues his “white period” with a cream seersucker suit, yellow tie, and brown suede loafers.

This close up reveals the fabric in greater detail. A micro grid pattern on his shirt, and the blue striping on his suit. Like Wes’ films, the devil is in the details.

Wes and his cast attend the red carpet opening night before the film screens. From left to right: Jason Schwartzman, Adrien Brody, Wes, Roman Coppola, & Bill Murray.

This close up reveals the hidden detailing on Wes’ outfit. The straight formal label on his jacket is more visible, and the burgundy bowtie appears to be of a fuzzy velvet material.

At the festival, The Darjeeling Limited played alongside Joel & Ethan Coen’s No Country for Old Men, and Marjane Satrapi & Vincent Paronnaud’s Persepolis.

Audio recording sessions for The Fantastic Mr. Fox began in October of 2007. In the above video, we see footage of these sessions that include a bevy of Wes outfits during this period that solidify his predilections for collared shirts and ties when directing.

There are other standout moments, like when Wes acts for the camera to give animators an idea of how the movement and blocking will be.

At a press conference to promote There Will Be Blood, Paul poses with his star Daniel Day-Lewis at the Four Seasons garden in Beverly Hills. 

Paul again keeps it casual with a brown cotton shirt, two buttons open, and blue trousers. A casualness almost rivaled by Day-Lewis’ green flannel, tattoos, and wrist accessories.

Kicking off the awards circuit, Paul and Daniel Day-Lewis attend the Los Angeles Film Critics Awards where There Will Be Blood is nominated for seven awards (including best picture and best director).

Where Day-Lewis opts for a striped suit-solid shirt scheme, Paul inverts it with a solid suit-striped shirt combo. No tie, obviously, since there’s no use trying when you’re standing next to Daniel Day-Lewis in that suit – even Wes would blush.

LOS ANGELES, CA – JANUARY 12: Director Paul Thomas Anderson arrives at the 2007 LA Film Critic’s Choice Awards held at the InterContinental on January 12, 2008 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)

This close up gives greater detail on the chocolate suede suit that Paul wears for the event. We also see the blood red and black oil striping of his shirt as well.

There Will Be Blood premieres at the Ziegfeld Theater in New York City in December of 2007. Pictured here is Paul with his wife Maya Rudolph, power-coupling it up on the red carpet.

They both wear matching black pea coats in a mostly monochromatic color scheme, complementing both the shadowy images in the film and on the poster behind them. Paul finishes off his red carpet look with some casual brown shoes, and an olive tie. Simple and spartan, not unlike the main character of Daniel Plainview himself.


Director Paul Thomas Anderson (R) and guest arrives at the 2008 AFI Luncheon held at the Four Seasons Hotel on January 11, 2008 in Los Angeles, California. (Photo by Steve Granitz/WireImage)

With the awards season underway, Paul attends the American Film Institute Awards Luncheon in January of 2008 with the producing partner on all his films, JoAnne Sellar.

There Will Be Blood is included on AFI’s Top Ten list along with Jason Reitman’s Juno and Sidney Lumet’s Before the Devil Knows You’re Dead.

The casualness of the event finally overlaps with Paul’s preferred sartorial speed, and yet he still manages to be even less formal than that by wearing this indescribable red hat. 

Director Paul Thomas Anderson arrives at the 2008 AFI Luncheon held at the Four Seasons Hotel on January 11, 2008 in Los Angeles, California. (Photo by Steve Granitz/WireImage)

A closer look of the red hat. Is it a beanie? Is it a trilby? Who knows, but it’s Proto-Paddington sheik.

At the 60th Director’s Guild Awards “Meet the Nominees” conference, Paul takes a page from Wes’ wardrobe and scarfs up for the event. 

The scarf is layered over a v-neck sweater, red/blue flannel, and navy shirt underneath. For bottoms, he’s wearing stonewash denim jeans and a brown belt.

Paul stands with his fellow director nominees: (from left to right) Paul, Julian Schnabel (The Diving Bell & The Butterfly), Joel Coen (No Country For Old Men), Tony Gilroy (Michael Clayton), Ethan Coen (No Country).

Director and Q&A moderator Jeremy Kagan photobombing. His bald head blessed with the touch of Paul’s finger.

This image from the Q&A offers a glimpse of Paul’s footwear: a pair of brown/tan casual boots.

A press conference before the DGA awards show holding his nomination plaque for Best Director. 

This time, Paul has dressed in suit and tie for the occasion. Navy blue with pinstriping, white grid patterned shirt, and black tie. 

The award for Best Director would go to Joel & Ethan Coen for their work on No Country For Old Men.

Paul at a luncheon photocall for the 80th Academy Awards. There Will Be Blood is nominated for seven awards, including Best Director.

Paul stands with his fellow director nominees. From left to right: Joel Coen, Paul, Julian Schnabel, Tony Gilroy, Ethan Coen, & Jason Reitman (Juno).

Close up on Paul. The same red flannel from the DGA nominees event is dressed up more with a black suit jacket.

Also of note, is the name tag showing the categories that Paul himself is nominated in: Best Picture, Best Screenplay, and Best Director.

Before the Oscars, Paul detours to attend the Berlin Film Festival in February of 2008 where There Will Be Blood has been accepted in the main competition. 

He wears a pale navy military-style coat, striped sweater, dark wash jeans, and a simple brown leather shoe.

Paul’s “Star Portrait” from the festival.

A shot of the striped sweater without the coat.

At the actual awards show, Paul wears a simple black suit and tie instead of a tuxedo. There Will Be Blood would win two Silver Bear awards, for Best Directing and Outstanding Artistic Contribution in Music.

The Festival’s top Golden Bear prize would go to Tropa de Elite by José Padilha.

One short week later, Paul and Maya Rudolph attend the red carpet of the 80th Academy Awards show. There Will Be Blood is up for seven awards, including best director for Paul.

This being Paul’s third time attending the Academy Awards, he solidifies his status as a tuxedo guy with yet another classic penguin suit look. However this tuxedo is clearly a product of the changing cultural tastes around menswear. The jacket is cut far closer to the body than previous tuxedos, and the trousers have a more distinct break in the cuff. No fuss, no muss.

There Will Be Blood would win two Oscars that night: Best Actor for Daniel Day-Lewis & Best Cinematography for Robert Elswit. 

Best Picture and Best Directing would both go to Joel & Ethan Coen for No Country For Old Men.

Shortly after the film’s release, Wes is approached by clothing designer APC for a branded merchandise collaboration for The Darjeeling Limited. 

Two designs were made and sold in limited markets.


Director Wes Anderson with Mr. Fox at “The Fantastic Mr. Fox” press conference at the Dorchester Hotel on October 14, 2009 in London, England. (Photo by Vera Anderson/WireImage)

Wes premieres Fantastic Mr. Fox at the 53rd British Film Institute Festival in London in October of 2009. 

In an uncanny resemblance to his Mr. Fox puppet, Wes wears an orange corduroy suit, beige sweater vest, and blue shirt.

At a photocall, Wes poses with the rest of his cast and crew from the film. From left to right: Wallace Wolodarsky, George Clooney, Wes, Bill Murray, Jason Schwartzman, Jarvis Crocker, & Wes’ brother Eric Anderson.

Visible in this photo are Wes’ matching orange wallabees.

For the red carpet premiere, Wes switches to a velvet black suit, pink, and matching velvet bow tie.

Here, Wes poses with Felicity Dahl, the widow of “The Fantastic Mr. Fox”’s author Roald Dahl.

Close up of shirt and bowtie details. What looks to be pink from afar, is actually a red micro grid check pattern.

HOLLYWOOD – OCTOBER 30: Director/co-writer/actor Wes Anderson and actor Eric Chase Anderson arrive at the AFI FEST 2009 premiere of 20th Century Fox’s “Fantastic Mr. Fox” held at Grauman’s Chinese Theatre on October 30, 2009 in Hollywood, California. (Photo by Kevin Winter/Getty Images for AFI)

Wes and his brother Eric at the west coast premiere of Fantastic Mr. Fox at AFI Fest. Clearly the suits and bowties run in the family.

This time, Wes keeps his color palette more subdued with a grey wool suit, green micro check shirt, and green tie.

This full body shot shows Wes again in his tan wallabees in lieu of traditional formal shoewear – another piece of his prep-casual armor.

Fantastic Mr. Fox would open in theaters by Thanksgiving of 2009 to much acclaim; its animation and musical score would be recognized with two Academy Award nominations. Not a bad way to end the decade.


In the next decade, both Andersons would enjoy a certain creative freedom based on the success of their films in the 2000s. This creative freedom would bring with it a new freedom of style as well, one that will be looked at in more detail on the next installment of The Fashionable Andersons.


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