Robert Redford as Jack Weil, smooth gambler and U.S. Navy veteran
Santa Clara, Cuba, December 1958
Release Date: December 14, 1990
Director: Sydney Pollack
Costume Designer: Bernie Pollack
Extending #CarWeek to get to casual Friday gives us the opportunity to pay tribute to Robert Redford’s classic casual warm-weather attire behind the wheel of a grand Cadillac convertible from the fabulous ’50s. The film in question is, of course, Havana, Sydney Pollack’s 1990 paean to Casablanca that starred Redford as Jack Weil, a cynical American gambler who finds love in the form of Cuban revolutionary Roberta “Bobby” Duran (Lena Olin) on the eve of that country’s revolution.
A man of unapologetically luxurious taste, Jack takes his Cadillac with him to Cuba and ends up motoring this opulent convertible out of the titular capital city to Santa Clara in search of the fugitive Bobby, hoping to convince her to flee the country with him and hoping to finance their escape with the diamond that he had long ago sewn into his arm.
What’d He Wear?
After spending much of his time hopping between casinos and bars in his colorful suits and sports coats, Jack Weil dresses down in a simple shirt and slacks for his romantic rescue mission. The silky blue shirt was no doubt made by Anto Beverly Hills, then known as Nat Wise of London, who had been Redford’s preferred shirtmaker on- and off-screen since the early years of his career. The shirt fastens up the plain front with tonal sew-through buttons, and each sleeve closes over the cuff with a single button on a pointed tab.
This soft silk shirt has a wide camp collar that is often referred to as a “Cuban collar” by clothiers like Scott Fraser Collection and is—in this case—a particularly appropriate moniker given the film’s setting. A small loop on the left side of the collar ostensibly connects to a small button under the right collar leaf that would button the shirt up to the top, though Redford wears the shirt more comfortably open at the neck. Both patch pockets on the shirt’s chest are covered with flaps with no buttons to close.
Jack wears the same tobacco brown trousers that he had previously worn for the dressier outfit of a cream linen sports jacket and light blue dress shirt. These trousers rise to the natural waist and have single reverse-facing pleats on each side of the fly and pockets along the side seams. Through the trouser belt loops, dropped about a quarter-inch from the top of his waistband, Jack wears an inch-wide dark brown leather belt with a gold rectangular box-style buckle. The bottoms of Jack’s trousers are finished with turn-ups (cuffs), which—like pleats—enjoyed more popularity during the fifties than some other decades.
Despite the relatively conservative outfit (when compared to items like his brushstroke-printed tie), he still wears a pair of spectator shoes, albeit a more subdued pair in walnut brown leather and tan nubuck that offer a softer visual contrast than the black-and-white correspondents that he wore with his blue dupioni silk sports coat. As identified by an auction listing, these five-eyelet wingtip oxfords were made by Bragano. Jack wears them here with black ribbed socks.
Jack wears a pair of large gold-framed aviator-style sunglasses with dark lenses, possibly a product of Ray-Ban. Originally developed for American military pilots in the late 1930s, the aviator is a suitable choice for Jack Weil with his military background and adventurous spirit.
Even when not spending late nights in a casino, Jack wears the gold jewelry and accessories emblematic of his gambler lifestyle, including his all-gold wristwatch and the gold signet ring on his right pinky that has seemingly replaced the actor’s own silver ring that he has worn on the third finger of his right hand in most of his movies since receiving it as a gift from the Hopi tribe in the late 1960s.
This type of shirt appears to be a favorite of Jack’s, as he later wears one in beige silk—with the same brown trousers, two-tone shoes, and gold accessories—upon returning to Havana.
The overall look of the beige flapped-pocket shirt with the brown slacks presents the effect of a military uniform, making it particularly suitable for Jack’s final on-screen outfit before leaving Cuba, illustrating his transformation from a cynical gambler to invested revolutionary sympathizer.
In mid-century America, few material possessions signified status so much as a Cadillac, and the wealthy Jack Weil would be well aware of this as he cruises along the Cuban coastline behind the wheel of his silver 1955 Cadillac Eldorado convertible.
A symbol of premium luxury, the Cadillac Eldorado was added to the marque’s lineup for the 1953 model year in commemoration of Cadillac’s golden anniversary. The name evokes El Dorado, the mythical South American “lost city of gold” that intrigued generations of explorers.
The Eldorado convertible was Cadillac’s top-of-the-line offering upon the model’s introduction in 1953, sharing the same 331 cubic-inch V8 as Cadillac’s entry-level Series 62 but commanding a price of $7,750 (nearly $75,000 in 2019 dollars), available only as a special-bodied convertible designed by Harley Earl. Only 532 were produced and sold during that first year.
For the following year, Cadillac settled the Eldorado into more of a standard production car, differentiated more by added trim than a unique body style, sacrificing this exclusivity for more accessible prices and, thus, nearly quadrupled sales from the ’53 model. Sales almost doubled with 3,950 units sold in 1955, the same year that Cadillac added its elegant and now-iconic tailfins to the Eldorado’s rear end.
1955 Cadillac Eldorado
Body Style: 2-door convertible
Layout: front-engine, rear-wheel-drive (RWD)
Engine: 331.1 cubic inch (5.4 L) Cadillac OHV V8 with Rochester 4-barrel carburetor
Power: 270 hp (201 kW; 273 PS) @ 4800 rpm
Torque: 345 lb·ft (468 N·m) @ 3200 rpm
Transmission: 4-speed GM Hydra-Matic automatic
Wheelbase: 129 inches (3277 mm)
Length: 223.2 inches (5669 mm)
Width: 79.8 inches (2027 mm)
Height: 61 inches (1550 mm)
The second generation of the Cadillac Eldorado concluded with the 1956 model year when the body was shortened by an inch but slightly widened out to an 80.1-inch wingspan. For the first time, a hardtop model was introduced and Cadillac began differentiating its two Eldorado options as the “Eldorado Biarritz” (convertible) and the “Eldorado Seville” (coupe).
The Eldorado remained in continuous production, evolving over five decades before General Motors announced that the Eldorado would cease production in 2002, appropriately the 50th anniversary of the very model it introduced for Cadillac’s own 50th anniversary.
How to Get the Look
Jack Weil proves that dressing down doesn’t mean sacrificing elegance, donning a simple outfit of a blue shirt and brown trousers resplendent with ’50s details like a wide camp collar and flapped shirt pockets, pleated and cuffed slacks, and spectator shoes that elevate an otherwise basic ensemble into something more interesting.
- Blue soft silk long-sleeve shirt with wide “Cuban” camp collar, two flapped patch pockets, and pointed-tab button cuffs
- Tobacco brown reverse-pleated trousers with dropped belt loops, straight/on-seam pockets, and turn-ups/cuffs
- Dark brown leather belt with gold rectangular box-style buckle
- Brown two-tone leather five-eyelet wingtip spectator oxfords
- Black ribbed socks
- Gold wristwatch with round gold dial on flat bracelet
- Gold signet pinky ring
- Gold-framed aviator sunglasses with dark blue-gray lenses
Do Yourself a Favor and…
Check out the movie.
I came 200 miles after you without a cigarette.