Today in 1915, the world welcomed the birth of Francis Albert Sinatra. To commemorate what would have been Frank’s 97th birthday, here is another focus on the original Ocean’s Eleven.

Vitals

Frank Sinatra as Danny Ocean, smooth-talking con man and casino heister

Las Vegas, New Year’s 1960

Film: Ocean’s Eleven
Release Date: August 10, 1960
Director: Lewis Milestone
Costume Designer: Howard Shoup
Tailor: Sy Devore

Background

Although not as technologically savvy (and sometimes quite cornier) than its 2001 remake, the original Ocean’s Eleven is a classic piece of nostalgia that transports viewers back to the good old days of guys in good suits drunkenly enjoying themselves in Vegas while blowing through countless broads, dames, and cigarettes.

The plot is basic: a team of eleven guys will rob five casinos on New Year’s Eve in Las Vegas. We already covered Sinatra’s gray specked sport coat during the planning phase. During the actual execution, Sinatra dresses a little sleeker, with a sharp dark suit and silk tie.

There are many stories about the film’s origins, but it is definitely the brainchild of Las Vegas gas station attendant Jack Golden Russell. According to one story, Russell handed the script to Sinatra while the latter was refilling his car at Russell’s station. In another more probable situation, Russell told director Gilbert Kay his idea. Kay then relayed it to Peter Lawford, who bought the rights in 1958 and imagined William Holden in the lead. After Sinatra became interested, he joked, “Forget the movie, let’s pull the job!”

What’d He Wear?

Sinatra sports this dark two-piece suit a couple times in the film, once when recruiting Vince Massler from the Phoenix burlesque club where Vince’s wife performs (!) and during the film’s climactic New Year’s Eve casino robbery as Sinatra empties the vault at the Sands.

Likely tailored by the Rat Pack’s preferred cutter Sy Devore, this charcoal suit with its subtle black tonal overcheck has a single-breasted ventless jacket with notch lapels that roll to the top of a three-button front and jetted hip pockets for a minimalist, Jet Age aesthetic. The single-pleated trousers have turn-ups (cuffs) on the bottoms, which break high over his black leather plain-toe derby shoes and thin black dress socks.

When recruiting Vince and downing a highball or two at the burlesque club, Sinatra wears a white shirt with a long point collar and button cuffs. After getting into a bar fight and running out of the club, the shirt collar points fall outside the suit and drape over the lapels. (When he needs to look good later on, Sinatra ensures that his collars stay in place.)

With the shirt, he wears a black textured silk necktie and black rounded square cuff links, which he wears several times in Ocean’s Eleven. He finalizes the look with a red silk pocket square that has a light red and yellow paisley center. Ever the artiste, Sinatra wears his pocket square puffed rather than folded.

For his night out in Phoenix, Sinatra looks like a cool and slightly dandified Reservoir Dog.

The black-on-charcoal suit is next seen on New Year’s Eve, when Sinatra and the gang are preparing to take down five Vegas casinos at the stroke of midnight. For this, Sinatra dresses up the black suit with a nicer shirt with tab collar – fastened by a gold collar pin – and double cuffs.

Tab collars are a British development, introduced by the fashion-forward Prince of Wales, Edward VII. After its height in the 1920s and 1930s, tab collars were briefly revived during the Mad Men era, circa 1960, and died out with a whimper and an attempted comeback in the early 1990s. They may be on their way back after Daniel Craig sported them in the latest James Bond outing Skyfall, although Craig wore his with a button tab rather than a traditional stud or a collar pin as worn by Sinatra and Remington Steele.

The benefits of a tab collar or collar pin? The neat, elegant arch of pushing the tie away from the neck. The worst part? Tab collar shirts must be worn with a tie and look very silly if the tie is loosened.

The narrow silk tie Sinatra wears with his collar pin has a small white and black checked pattern, appearing silver from a distance. Again, he wears his usual black cuff links. In a minor continuity error, Sinatra’s cuff links are rounded squares during scenes filmed in the studio and are simple squares during scenes filmed actually in Vegas.

With his fancier collar and tie, Sinatra foregoes the pocket square. Perhaps it would have gotten in the way while robbing the safe?

Also during this scene, we get a rare and brief glimpse at his wristwatch. We can hardly see it, but it appears to have a squared white face on a dark leather strap.

Go Big or Go Home

Although Sinatra plays a character named Danny Ocean, he is basically playing Sinatra in the film. He keeps his cool as he leads his charming group of cads in Vegas. Along the way, he romances a few beautiful women who end up leaving him in the end through no perceived fault of his own. All in all, this was Frank Sinatra’s life in 1960.

As the holidays are approaching, now is the time to grab two or three of your buddies, style up in suits, and have a few drinks for Frank. He may not have led the life of a role model, but he sure knew how to look good and have a fun time.

To celebrate the upcoming Christmas season (and to channel the heisters’ instructions in the film to sing “Auld Lang Syne” during the robbery), here is a classic rendition from Frank and Dean.

What to Imbibe

As usual for Sinatra during Ocean’s Eleven, he is drinking a highball in the scene where he and Peter Lawford’s character recruit Vince at the burlesque bar. For more on Sinatra’s highballs, check out the Jack & Soda breakdown in my previous Sinatra post.

Frank also has his trademark unfiltered Camels that were buried with him in his casket (as well as a bottle of Jack Daniel’s).

Interestingly, Sinatra had done ads for Chesterfield cigarettes in the late 1940s through the early 1950s. Just after this, his voice began to suffer and his career took a steady decline after his vocal cords hemorrhaged on stage during a show at the Copacabana in April 1950. Things got worse – his relationship with Ava Gardner soured (they got married) and he was dropped by Columbia Records. Then, famously portrayed by Al Martino as Johnny Fontaine in The Godfather, he got his Academy Award-winning part in From Here to Eternity, he recorded a stellar album with Nelson Riddle at Capitol, and by 1953 he had the world on a string. He was also now seen smoking Camels. Did Sinatra blame Chesterfields for nearly ruining his career? Smoke Camels, kids.

How to Get the Look

Sinatra’s dark-as-night suit, white shirt, and tie are a classic look copied in countless additional heist films, including The Getaway in 1972, Reservoir Dogs in 1992, and Heat in 1995. Sinatra just puts his own spin on it with a black overcheck, patterned ties, collar pin, and a pocket square.

• Charcoal (with black overcheck) Sy Devore-tailored suit, consisting of:
  • Single-breasted 3-button jacket with notch lapels, welted breast pocket, jetted hip pockets, 3-button cuffs, and ventless back
  • Single-pleated trousers with turn-ups/cuffs
• White dress shirt with tab collar and double/French cuffs
  • Rounded square black cuff links
• Black textured silk tie
  • …or a narrow white-and-black mini-checked silk tie
• Black leather plain-toe derby shoes
• Black dress socks
• Gold collar pin
• Red silk pocketsquare with a light red and yellow paisley center pattern, puffed in the breast pocket
• Wristwatch with a square white face and dark leather strap

Do Yourself a Favor and…

Check out the movie.

The Quote

Not from the film itself, but very indicative of Sinatra the man…

The best revenge is massive success.