Once Upon a Time in Hollywood: Brad Pitt in Black and White

Brad Pitt as Cliff Booth in Once Upon a Time... in Hollywood (2019)

Brad Pitt as Cliff Booth in Once Upon a Time… in Hollywood (2019)


Brad Pitt as Cliff Booth, swaggering Hollywood stuntman

Los Angeles, Summer 1969

Film: Once Upon a Time in Hollywood
Release Date: July 26, 2019
Director: Quentin Tarantino
Costume Designer: Arianne Phillips

WARNING! Spoilers ahead!


Tonight the night? Why not?

When Cliff Booth poses himself this question on the night of Friday, August 8, 1969, he was merely considering whether or not he should partake in an acid-dipped cigarette he bought from “a hippie girl” six months earlier, but the night turns out to be far more eventful than a mere drug experiment.

Brad Pitt may have asked himself the same question a month ago during the 92nd Academy Awards when he won his first Oscar for acting in recognition of his performance in Once Upon a Time… in Hollywood, the ninth film from Quentin Tarantino as the auteur added his own revisionist touch to a consequential year for American pop culture.

As today is Friday the 13th, let’s take a look at one of Cliff’s less celebrated outfits on what started as a very unlucky night for the stuntman… until he turned the tables thanks to that acid-dipped cigarette, his pet pit bull Brandy, and a few decades worth of combat-honed grit.

What’d He Wear?

While his movie star pal Rick Dalton (Leonardo DiCaprio) has at least three costume changes over the course of the day, Cliff sticks with the same duds he wore when flying back from Italy for his day’s errands and the evening’s dinner and subsequent drinks with Rick. Characteristic for Cliff, it’s a relatively utilitarian and simple outfit, if a flashier alternative to the blue denim trucker jacket and jeans he wore with his black tee for the movie’s first scene.

Made from a tightly woven white cotton twill, Cliff’s trucker jacket is otherwise consistently styled like the traditional Levi’s® “Type III” that has been a casual staple for men and women over the better part of a century. Cliff’s white jacket has six silver-toned rivet buttons up the front from the waist hem to the shirt-style collar, a more traditional trucker jacket detail than the zip-front of his blue denim Wrangler jacket from the opening scene.

The jacket also has two chest pockets that each close with a single button through a pointed flap, no hand pockets, and buttoned cuffs. There are two short tabs, each placed toward the back on each side of the hem, that fasten to one of two buttons to adjust the tightness around the waist.

Cliff gleefully picks up Brandy after having to spend six months away.

Cliff gleefully picks up Brandy after having to spend six months away.

Cliff’s jacket may indeed be a Levi’s product, albeit with the distinctive red tag removed from the left pocket, and Levi’s still offers its Original Trucker Jacket in a white “steel hour” cotton denim (via Amazon or Levi’s). If you’re uncomfortable with going all-white, I also recommend the creamy “muslin” cotton canvas trucker jacket from J. Crew Mercantile (via Amazon), owned by yours truly which has proven to be a comfortable, lightweight layer in the summer.

When stripped down to just his black T-shirt and white jeans, Cliff’s outfit echoes what Sharon Tate (Margot Robbie) wore to the movies earlier in the film and was photographed wearing for much of Once Upon a Time… in Hollywood‘s promotional material.

Black T-shirts can range from less than $10 when purchased from the likes of Gildan, Hanes, H&M, and Uniqlo, up to around $100 from fashionable brands like James Perse (as favored by Hank Moody), Rag & Bone, and Sunspel. (There are likely companies selling plain black T-shirts for much more than that, but… come on.) A no-frills guy like Cliff would likely opt for the less-expensive end of the spectrum and, as GQ has observed, that wouldn’t be far from Brad Pitt’s own wheelhouse.

The black cotton T-shirt has a classic crew neck and short sleeves that flatter Cliff’s athletic physique.

"Uh... can I help you?"

“Uh… can I help you?”

Cliff returns from Rome wearing white jeans rather than his usual (and more characteristic) blue jeans. Why the switch? Perhaps to indicate some success, his BDE (it takes a bold man to wear white jeans), and to serve the narratively functional purpose of providing a clean palette for his blood to contrast against after he takes a knife to the hip during his fight with the crazed Manson family killers who show up at Rick’s doorstep.

The white jeans are likely cotton or an era-specific cotton/polyester blend, woven in a hairline-thin ribbing rather than the diagonal twill seen on most denim. Cliff’s pants are otherwise identically styled like traditional jeans with a five-pocket layout (including a coin pocket on the right side) and belt loops. His jeans are fitted through the hips and legs, slightly flaring out at the bottoms like a boot-cut.

If you’re looking to explore the world of white jeans, I identified a few potentials that could get you started:

  • Calvin Klein Men’s Slim Fit Jeans in “Nantucket white” 98% cotton/2% elastane stretch blend (via Amazon)
  • Goodthreads Men’s Standard Slim Fit Jeans in white “vintage” 98% cotton/2% elastane stretch blend (via Amazon)
  • Levi’s 541 Athletic Fit Jeans in “white bull denim” 99% cotton/1% elastane stretch blend (via Amazon or Levi’s)
  • Tommy Hilfiger Men’s THD Slim Fit Jeans in “snow white” 98.5% cotton/2.5% elastane stretch blend (via Amazon)
Despite being held at gunpoint and considerably under the influence, Cliff's stunt training, war experience, and trusty pal Brandy gives him the upper hand against the jittery Tex.

Despite being held at gunpoint and considerably under the influence, Cliff’s stunt training, war experience, and trusty pal Brandy gives him the upper hand against the jittery Tex.

Cliff’s familiar Stuntman’s Association Member belt buckle, a large brass oval with an embossed film camera in the center, is now worn on a python snakeskin belt, a distinctive touch that is certainly flashier but still consistent with his cowboy image and persona. (For an earlier look at Brad Pitt in snakeskin, check out the custom Anto shirt he wore at the end of Ocean’s Eleven!)

Real snakeskin belts like this matte python belt from W. Kleinberg (via Neiman Marcus) tend to be expensive, but you can also evoke the look with a snakeskin-effect belt like this affordable calfskin belt from LATICCI (via Amazon) or this reversible snakeskin-printed belt from I.N.C. (via Macy’s).

Acid-dipped cigarette or not... that's gotta hurt.

Acid-dipped cigarette or not… that’s gotta hurt.

Brad Pitt on the Once Upon a Time... in Hollywood set (Photo by SplashNews.com)

Brad Pitt on the Once Upon a Time… in Hollywood set (Photo by SplashNews.com)

Cliff has also traded in his comfortable moccasin boots for a pair of equally on-brand engineer boots in a unique taupe lightly napped leather. The boots have hard dark brown leather soles and straps across the vamps with a hefty steel single-prong buckle.

These hard-wearing engineering boots had been originally developed in the 1930s for firemen on steam locomotives (that kind of engineer) and eventually became a favorite of the motorcycle subculture, worn by rebellious ’50s icons like Marlon Brando in The Wild One and James Dean in Rebel Without a Cause.

Finding engineer boots for men in this fawn-like leather is difficult, though brown boots abound like these Harley-Davidson “Brendan” 10-inch boots (via Amazon). For a different approach, Chippewa makes a sand-colored suede 11″ steel-toed engineer boot (via Chippewa) that may not be screen-accurate but would bring unique panache to an outfit.

Another detail indicating how much Cliff has changed are his sunglasses as he’s now wearing a pair of large gold rectangular frames, more like the glasses often associated with 1970s Elvis than the classic aviators he had been wearing six months earlier.

While Cliff may be diverting from his usual jeans, boots, and accessories (he isn’t wearing the corded bracelets on his right wrist either!), one item he hasn’t switched out is the gold-toned Citizen 8110 wristwatch that he wears on a brown leather 1 5/8″-wide cuff custom-made for Pitt by Red Monkey Designs.

Cliff's Bloody Mary gives him a more comfortable ride in coach.

Cliff’s Bloody Mary gives him a more comfortable ride in coach.

Though the screen-worn Citizen is vintage, the 8110 model itself wasn’t introduced until the 1970s as Citizen’s response to Seiko’s earlier “bullhead” design, and thus it’s technically an anachronism to see it on Cliff’s wrist. The 38mm case is gold-finished nickel with three black sub-dials and two top-placed pushers at 11:00 and 1:00, flanking the 12:00 crown and resembling bull horns… thus the “Bullhead” moniker.

What to Imbibe

From their respective seats in first class and coach, Rick and Cliff both drink Bloody Marys on their way back to Los Angeles from Italy, though Rick’s isn’t served to him as he’s forced to mix his own “bottomless Bloody Mary” with mini bottles of Stoli and canned tomato juice.

“The only thing the two men know of for sure? Tonight, Rick and Cliff will have a good old-fashioned drunk. Both men know once the plane touches down in El Segundo, it’ll be the end of an era for both of them. And when you come to the end of the line with a buddy who is more than a brother and a little less than a wife, getting blind drunk together is really the only way to say farewell,” narrates Kurt Russell.

The party begins at Casa Vega, a Mexican restaurant in the San Fernando Valley, where both Rick and Cliff drink more than a few Margaritas and make the responsible decision to take a cab rather than drive home.



So what’s the secret to a perfect Margarita? When he drunkenly stumbles home, Rick opts to mix some up in his blender—hilariously drinking from it as he barks at Tex’s loud car outside—but I try to stay away from frozen margs, sours mix, or anything that smacks of mass production for cheap consumption.

My trusted copy of Mr. Boston Official Bartender’s Guide advises 1.5 ounces of tequila, 0.5 ounces of triple sec, and one ounce of lemon or lime juice, shaken with ice and strained into a chilled, salt-rimmed cocktail glass. In The Gentleman’s Guide to Cocktails, Alfred Tong gets more specific and changes the ratio, calling for two ounces of white tequila, one ounce of Cointreau, and one ounce of lime juice, prepared similarly. I also like the creativity of “the only margarita recipe you’ll ever need”, according to liquor.com, which maintains Tong’s ratio but splits the ounce of Cointreau into a half-ounce of orange liqueur and a half-ounce of agave syrup.

Personally, I like to use the following, borrowing a ratio from Aliza Kelly Faragher in The Mixology of Astrology:

  • 2 ounces of 100% agave silver tequila
  • 1 ounce of Cointreau
  • 3/4 ounces of fresh lime juice

With the margarita glass chilling, I mix that concoction with plenty of ice, then salt the rim of the glass, strain in the margarita, and finish it off with a slice of lime to garnish. (I’ve also experimented with “rinsing” the glass first with mezcal for a smoky touch. Recommended for me, not necessarily for all.)

How to Get the Look

Brad Pitt and Leonardo DiCaprio on the set of Once Upon a Time... in Hollywood (2019)

Brad Pitt and Leonardo DiCaprio on the set of Once Upon a Time… in Hollywood (2019)

Cliff Booth’s nearly matching white trucker jacket and jeans for this sequence create the effect of a leisure suit, which would prevail as one of the more unfortunate men’s fashion trends over the following decade. As Brad Pitt wears it better than most should, I’d recommend taking cues from the individual pieces in Cliff’s ensemble, building upon the neutral foundation of a plain black T-shirt to experiment with white denim rather than traditional blue, whether that means swapping out the jeans or the jacket.

  • White cotton denim trucker jacket with shirt-style collar, six rivet buttons, two chest pockets (w/ single-button pointed flap), button cuffs, and button-tab side hem adjusters
  • Black cotton crew-neck short-sleeve T-shirt
  • White thin-ribbed cotton jeans with belt loops, five-pocket layout, and slightly flared boot-cut bottoms
  • Python snakeskin belt with large brass Stuntman Association Member belt buckle
  • Taupe suede leather engineer boots with steel-buckled vamps
  • Gold rectangular-framed aviator sunglasses with wide arms
  • Citizen 8110 Bullhead gold-finished nickel watch with 38mm “bullhead” case, gold dial with three black sub-dials, and custom brown leather cuff strap

Do Yourself a Favor and…

Check out the movie.

The Quote

And away we go…!


  1. cox1961

    I loved what Brad wore in this movie. He looked gorgeous. Especially the white jeans, white trucker jacket and black t shirt – nice!

  2. George

    I thought it was a very McQueen inspired look. Actually earlier in the movie in the scene at the Playboy mansion Damian Lewis as McQueen is wearing white 5 pocket pants. In the early 70s McQueen wore jeans and denim jacket a lot. Here at Bruce Lee’s funeral https://www.bing.com/images/search?view=detailV2&id=6685CB90EBA5F7CA99930D230F871A2ED9B407F5&thid=OIP.BQcFzclJku4_TEk5ebO9NAAAAA&mediaurl=https%3A%2F%2Fi.pinimg.com%2F236x%2F0a%2Fd7%2Fdd%2F0ad7dd35097280c8413452c556bb7e03–bruce-lee-funeral.jpg&exph=214&expw=236&q=steve+mcqueen+at+bruce+lees+funeral&selectedindex=6&ajaxhist=0&vt=0&eim=1,2,6&ccid=BQcFzclJ&simid=608016881605282445&sim=11

  3. jdreyfuss

    I usually mix a margarita (and any other “flower” sour) in a traditional sour ratio of 2.5 oz. liquor, 1.5 oz. lime or lemon juice, and 1 oz orange liquer. For a margarita or daiquiri it’s lime juice and triple sec. For a sidecar or kamikaze it’s lemon juice and Cointreau.

    In the photo you have his jacket looks more like a plain weave than a twill weave. I have a cream Type III in a medium weight cotton lawn that’s not quite heavy enough to be canvas that Levi’s calls chambray, though the cream is too light for any end-on-end effects to be noticeable and white wouldn’t be mottled and would just be cotton lawn.

    Ralph Lauren offers jeans in a 3×2 cotton gabardine in both white (if you can keep them clean) and cream (if you can’t). I don’t know if they have it in a bootcut fit.

  4. Cody H Cromarty

    I actually imitated this look (with cowboy boots and no belt buckle) at work once and it was great.

  5. Pingback: Once Upon a Time in Hollywood: Leo's Black Airport Attire » BAMF Style
  6. Shawn M. Winterich

    The aloha shirt shown in February 1969 shows Cliff’s friendly and easygoing nature. Cliff takes off his white denim jacket, when he returns to Rick’s house Bev Hills from Italy six months later, exposing a black t-shirt over white jeans. I like to think of this as Cliff’s dark nature rising to the top as he ruthlessly faces off against several intruders.

    Cliff had fought Bruce Lee with not threat to life–not even hitting in the face–dressed in *white* shirt over *black* pants. (The damage to the Lincoln was a different story. NB: Obviously the damaged door was a retrofitted prop. A real Lincoln from the 1960s wouldn’t crumble like that.)

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