Marlon Brando as Sky Masterson, smooth gambler
Havana to New York, Spring 1955
Film: Guys and Dolls
Release Date: November 3, 1955
Director: Joseph L. Mankiewicz
Costume Designer: Irene Sharaff
On the traditionally unlucky day of Friday the 13th, we could all use a dash of lady luck, the concept popularized in the standard “Luck Be a Lady” that Frank Loesser had composed for the musical Guys and Dolls. Five years after Robert Alda had originated the song on stage in 1950, Marlon Brando overcame his own insecurities about his singing voice resembling “the mating call of a yak” to perform the song in Mank’s cinematic adaptation… much to the likely chagrin of his co-star Frank Sinatra, who would record it twice for his own Reprise Records label in the ’60s.
But before Sky Masterson asked lady luck to show him just how nice a dame she can be, he sets his sights on another doll, specifically the prim and pretty Sergeant Sarah Brown (Jean Simmons) of the Save-a-Soul Mission, whose organizational goals could not be more antithetical to all Sky holds dear. To win a bet with fellow gambler Nathan Detroit (Sinatra), Sky invites her to dinner in Havana, where Sister Sarah’s uncharacteristic Thursday night results in plenty of Bacardi and barfighting.
What’d He Wear?
They may call it lady luck, but Sky Masterson’s easy sense of style shows more intention than chance. The gambler has crafted a sleek signature style for himself, more contemporary with the ’50s image of gangsterdom than the flashier stripes of his pal Nathan. Subverting the time-tested formula of darker ties with white or blue shirts, Sky routinely wears light ties against dark shirts, swapping out his suits based on time of day: gray by day and dark blue at night.
Navy suits have long been an essential in men’s wardrobes, with their appeal even extending to a snappier dresser like Sky Masterson. But, like Sky’s gray suit, not just any conventionally styled suit would do. The single-breasted jacket of this dark navy gabardine suit builds Sky’s sleek—if somewhat intimidating—silhouette with fashionably wide padded shoulders. The wide notch lapels roll to a single button positioned low, even a few inches below the trouser waistband. The suppressed waist, ventless back, and narrow fit of the full-skirted quarters further emphasize the tapered figure created by the wide shoulders.
The patch pockets on the hips are each covered with a flap, with an additional flapped ticket pocket on the right side. Sky dresses the jacket’s welted breast pocket with a white linen pocket square, a more conventional choice than the kerchiefs he wears with his gray suit that were designed to match his shirts. The sleeves are finished with four-button cuffs.
The cut and details of Sky’s suit would ultimately differentiate it from most off-the-rack suits today, but—especially with a more conventional white shirt and tie—it would not have differed much from business suits of its era. Where Sky truly differentiates his style is with his offbeat choice of shirt and tie. I doubt that he even has a white shirt in his wardrobe, always opting for dark and silky shirts in colors that echo his suit.
With this suit, Sky exclusively wears a dark indigo shirt that’s just a shade lighter than the suiting, with a subtly silky finish suggestive of a high-twist cotton, a silk blend, or a blend with an “artificial silk” like viscose or rayon. The shirt has a long point collar, a plain front (no placket), and double (French) cuffs fastened with a set of gold oval links with black enamel faces.
Sky’s pale yellow silk tie provides the outfit’s only contrast against the fields of dark blue. Knotted in a tight four-in-hand, the tie features a spaced pattern of dark suns and moons. The sun shapes resemble children’s drawings of them, with a small circle surrounded by rays shooting out of it, while the moons are always positioned on their own line and portray last-quarter and waning-crescent phases.
The suit’s matching trousers are pleated and cuffed, consistent with the era’s prevailing fashions, with double reverse-facing pleats on each side and turn-ups on the bottoms that break cleanly over the tops of Sky’s black calf leather cap-toe semi-brogue oxfords, which he wears with dark socks (likely black or dark blue).
The trousers rise to Brando’s natural waist, where he holds them up with a set of plain gray fabric suspenders (braces) that have double sets of tonal leather “ears” hooking onto buttons along the inside of the trouser waistband and silver-toned adjuster hardware. Though Sky doesn’t wear a belt, he does make use of the trouser belt loops by looping the ring-end of his gold keychain to the forward-most belt loop on the right side and storing his keys in the trousers’ right-side pocket.
Sky typically likes to match his fedoras to his suits, though we see a brief exception as he holds his pearl-gray felt Royal Stetson fedora while dressed in his dark navy suit in Havana. Upon returning to New York, he swaps this out for a more tonally coordinated wide-brimmed fedora made from a dark navy felt with a matching grosgrain band.
Like many men of the era, Sky wears a pinky ring, in this case a substantial gold ring with a large smooth oval sapphire blue stone shining from the face.
Sky also dresses his left wrist with a gold watch, a subtle but unique timepiece with a recessed black round dial against the squared 14-karat gold case, secured on a black leather strap. I know that cosmetically similar watches were made during the era by Wittnauer, a New York-based watch company that had been purchased by Swiss brand Longines in 1950. Longines held onto the Wittnauer brand for nearly half a century before it was sold to Swatch in the 1990s and then again to Bulova, who continues producing Wittnauer brand watches to this day.
You can still find classic Wittnauer Geneve watches with these round dials inset against square gold cases on sites like eBay, as Longines seemingly produced this style from the 1950s through well into the ’80s.
In November 2020, Live Auctioneers auctioned a navy suit that had evidently been made for Marlon Brando to wear in Guys and Dolls, with a screenshot connecting it to this scene, though even a cursory comparison illustrates that the auctioned suit is much different. Instead of this suit’s notch lapels and patch pockets, the auctioned suit has peak lapels and jetted pockets, like a dark blue copy of the gray suit rather than the one featured in this sequence. It may indeed have been made for Brando to wear as Sky Masterson as the bias label suggests, but it did not appear in the finished film.
What to Imbibe
Though one could certainly call the nature of Sky’s bet with Nathan into question, Sky certainly begins navigating into morally questionable waters when he misleads the teetotaling Sister Sarah into enjoying a few too many boozy “milkshakes” while in Havana. She had insisted on only ordering milk, so Sky requests that the waiter bring “dulce de leche… dos.”
Sarah: What did you order?
Sky: Uh, dulce de leche… dulce is the Spanish word for “sweet”, de means “of”, and leche means “milk”.
Sarah: “Sweet of milk.” Don’t they serve it plain?
Sky: Well, uh, only in the morning, it has to do with the heat. At night, they put a kind of preservative in it.
Sarah: That’s interesting! What do they use?
Sarah: Bacardi? Doesn’t that have alcohol in it?
Sky: Well, just enough to keep the milk from turning sour.
The waiter brings out two loaded coconuts with straws, prompting the unsuspecting Sarah to proclaim “this is a tasty milkshake! You mind if I have another?”
Outside of Guys and Dolls, I believe that enjoying too much dulce de leche would result more in a stomachache than drunkenness, as it typically refers to a type of caramelized milk with a jam-like consistency, used to top sweet desserts and fruits. In the context of Sky and Sarah’s drunken adventures, I picture the concoction as a tropical approach to the Brandy Alexander, consisting of Bacardi rum, coconut milk, and crème de cacao.
Doing some investigating, I found that Colleen Graham at The Spruce Eats had discovered a recipe that Bacardi endorsed in 2009 around the revival of Guys and Dolls on Broadway that doesn’t stray too far from what I had imagined. The recommended ingredients would be:
- 1 ounce of light rum, preferably Bacardi
- 1/2 ounce of chocolate liqueur, like Godiva
- 1/2 ounce of sweetened condensed milk (or regular milk, cream, or half and half, for a less rich drink)
- Ground cinnamon and shaved chocolate, for garnish
Shake the rum, chocolate liqueur, and milk in an ice-filled mixer, strain into a chilled cocktail glass—or coconut—and garnish with the ground cinnamon and chocolate shavings on top. Simple to make, and even simpler to enjoy.
How to Get the Look
It may take some help from lady luck to pull off Brando’s bold gambler style from Guys and Dolls, but just follow the Night Sky sartorial philosophy of a midnight-hued suit and shirt illuminated by the pale moonbeam of a celestially patterned yellow tie splitting the center.
- Dark navy gabardine suit:
- Single-breasted, single-button jacket with wide notch lapels, welted breast pocket, flapped patch hip pockets with flapped ticket pocket, 4-button cuffs, and ventless back
- Double reverse-pleated trousers with belt loops, side pockets, jetted back pockets, and turn-ups/cuffs
- Indigo-blue silky shirt with point collar, plain front, and double/French cuffs
- Gold oval cuff links with black enamel-filled faces
- Pale-yellow sun/moon-patterned silk tie
- Gray fabric suspenders/braces with silver adjusters
- Black leather cap-toe semi-brogue oxford shoes
- Black socks
- Dark navy felt wide-brimmed fedora with dark navy grosgrain band
- Gold pinky ring with blue oval stone
- Gold square-cased wristwatch with round black recessed dial and black leather strap
Do Yourself a Favor and…
Check out the movie.