Once Upon a Time in Hollywood: Leo’s Black Airport Attire

Leonardo DiCaprio and Lorenza Izzo in Once Upon a Time in Hollywood (2019)

Leonardo DiCaprio and Lorenza Izzo in Once Upon a Time in Hollywood (2019)


Leonardo DiCaprio as Rick Dalton, re-energized movie and TV star

Rome to Los Angeles, Summer 1969

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


I recently had the good fortune to rejoin my friend Peter Brooker on his excellent podcast, From Tailors With Love, joined by John Williams of James Bond Radio to talk about the style in Once Upon a Time… in Hollywood, Tarantino’s ode to the movie industry at the close of the 1960s.

Though Once Upon a Time in Hollywood cycles through the orbit of real-life stars like Sharon Tate, Steve McQueen, the Mamas and the Papas, and James Stacy—to name just a few—the central story focuses on the dynamic between the fictional actor Rick Dalton (Leonardo DiCaprio) and his best friend, the laconic stuntman Cliff Booth (Brad Pitt).

The movie begins with Rick coming to terms with his “washed-up” career, his desperation leading to a meeting with talent broker Marvin Schwarz (Al Pacino), who suggests spaghetti westerns as the gateway to the next phase of Rick’s career. Following Rick’s impressive performances on episodes of The F.B.I. and Lancer, Schwarz books him four back-to-back gigs in Italy, where he also meets and marries the beautiful starlet Francesca Capucci (Lorenza Izzo) as his stardom climbs to new heights.

Following six months in Europe, Rick returns to Hollywood on the fateful night of Friday, August 8, 1969, via a Pan Am jet… though not pretending to be a pilot, as Leo’s characters have been known to do. Having packed on 15 pounds due to Italian carb-loading, Rick considers having to take the next step of his life without Cliff, who he can’t afford to continue paying as the expenses of his new life’s lifestyle seem to outweigh the financial windfall of his newfound success.

As Kurt Russell narrates before the jet alights at LAX:

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.

What’d He Wear?

During our From Tailors With Love conversation, John had mentioned that Rick Dalton’s traveling outfit was a highlight for him, which encouraged me to take another look. As opposed to Cliff, who spends the entire day in his black T-shirt with white jeans and jacket, Rick cycles through three different outfits on Friday, August 8, beginning with this primarily black garb consisting of a black jacket, shirt, trousers, and boots, with an added touch of color only from the natty scarf knotted around his neck.

The new outfit signals Rick’s transition from his years as a washed-up Western star, when he dressed in warm shades of brown, mustard, and orange. His leather jackets and turtlenecks had been certainly contemporary to the late ’60s but not as fashion-forward as the double disco collars and paisley scarf he wears when returning stateside with renewed swagger, ready to take on the ’70s.

Leonardo DiCaprio and Lorenza Izzo in Once Upon a Time in Hollywood (2019)

Despite the Bloody Marys, Rick finds himself unable to relax on the plane, bothered by considering the prospects of a future sans Cliff… and by his new wife’s snoring.

The decreasing formality of the ’70s revived the popularity of neckerchiefs and scarves, now worn as sporty alternatives to traditional ties. Rick’s scarf delivers the outfit’s only significant dash of color, patterned with an electric purple, magenta, and yellow paisley print against a black silk ground.

Rick wears the top of his black shirt open to comfortably keep the scarf knotted over his neck, allowing the ends of the scarf to rakishly fall over the front of his shirt. The long-sleeved shirt is subtly contrast-stitched with white threading around the long-pointed collar, buttonholes, and via sets of two thin stripes down each side of the front.

Leonardo DiCaprio and Lorenza Izzo in Once Upon a Time in Hollywood (2019)

While I don’t believe the jacket and trousers are made from matching fabrics, the look portends the infamous leisure suits that lined the closets of many a disco-era gent or—perhaps to an even greater extreme—a black jumpsuit like those made famous by Elvis Presley.

Rick’s hip-length jacket has a long-pointed collar echoing the shirt layered under it, and a brass zipper with a circular pull tab would close the front if he wasn’t wearing it open. The four pockets are each covered with a flap with a drooping “dog ear” in the center that fastens closed through a gold-toned bone-shaped clasp.

The black flat front trousers have a self-suspended waistband that closes through an extended two-button tab. The plain-hemmed bottoms have a decided flare, creating a dramatic sweep over his black leather plain-toe boots s he strides through LAX.

Leonardo DiCaprio and Lorenza Izzo in Once Upon a Time in Hollywood (2019)

Francesca’s red jumpsuit resembles an identical item worn by Megan Draper (Jessica Paré) in the Mad Men episode “The Better Half”, set in the late ’60s. Throughout the later seasons of Mad Men, the character of Hollywood-dwelling actress Megan invited comparisons to the real Sharon Tate, particularly after she appeared on the show wearing a white T-shirt with a red star that Tate had famously worn in real life.

On the verge of new stardom at the dawn of a decade celebrating excess, Rick has also upgraded his eyewear to a proto-Elvis style of oversized Carrera 549 sunglasses, with thick brown plastic frames that flare out around the bottoms of each lens and have wide, perforated gold arms, a style that even the more practical-minded Cliff has adopted. (The King himself was reported to pick up his first famous pair of “TCB” frames from Optique Boutique in 1970, per Barnebys.)

Rick continues wearing the jewelry that was custom-made for his character, including the double-sided pendant monogrammed “R” on one side and with a Tudor rose design on the other, per costume designer Arianne Phillips’ interviews with Collider and Fashionista. In the latter, Phillips also provided background for the chunky ring Rick wears on his right pinky, explaining that “the lion pinky ring was a collaboration with Chris Call, our property master, Leo and Quentin.”

Leonardo DiCaprio and Lorenza Izzo in Once Upon a Time in Hollywood (2019)

Rick’s lion-relief pinky ring flashes as he sets up the vintage Hopalong Cassidy mugs behind his bar. Interestingly, Hopalong Cassidy had been the childhood book of choice for Jay Gatsby, who DiCaprio had played several years earlier.

Rick also returns stateside with an additional ring… in the form of a plain gold wedding band on the third finger of his left hand.

Under the left sleeve of Rick’s jacket and shirt, we glimpse a dark brown alligator watch strap that suggests he’s likely still wearing the subdued 18-carat yellow gold Chopard Classic manual-winding watch.

What to Imbibe

“Looks delicious, thank you,” Rick comments to the Pan Am flight attendant that serves his Bloody Mary. He’s clearly getting the first-class treatment as the stewardess even dropped in his two olives herself, while Cliff had to mix his up farther aft with a can of tomato juice and some Stoli.

Leonardo DiCaprio and Lorenza Izzo in Once Upon a Time in Hollywood (2019)

Rick takes a refreshing slurp of his Bloody Mary.

Having emerged sometime during the interwar era—occasionally attributed to comedian George Jessel—the Bloody Mary’s basest ingredients are vodka and tomato juice, in varying proportions and with even more varying accoutrements that range from the traditional (celery stalks and Worcestershire sauce) to the avant-garde (lobster tails and burger sliders). The glassware tends to be of the longer variety, typically highball glasses with some opting for draft or even hurricane glasses, all with considerably more volume than the rocks glass that Rick’s Bloody Mary is served in.

How to Get the Look

Leonardo DiCaprio and Lorenza Izzo in Once Upon a Time in Hollywood (2019)

Leonardo DiCaprio and Lorenza Izzo in Once Upon a Time in Hollywood (2019)

Recently gain about 15 pounds (and a wife) during a six-month sojourn in Europe? They say black is slimming, so drape yourself in fashion-forward black from head to toe, with a touch of color knotted around your neck to assuage any sinister associations.

  • Black hip-length zip-up jacket with long point collar and four flapped pockets (with gold-clasp closure)
  • Black long-sleeved shirt with white contrast-stitched long collar, buttonholes, and double stripe sets
  • Black flat-front self-suspended trousers with 2-button extended waist tab, slanted front pockets, and flared plain-hemmed bottoms
  • Black leather plain-toe boots
  • Brown plastic oversized sunglasses with gold perforated arms
  • Gold “R”-monogrammed/Tudor rose pendant on thin gold necklace
  • Gold chunky lion-motif pinky ring
  • Gold wedding ring
  • Chopard Classic 18-carat yellow gold wristwatch with round white dial on brown alligator leather strap

Do Yourself a Favor and…

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