Suiting Up for Sinatra’s Birthday

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.

Frank Sinatra as Danny Ocean in 1960's Ocean's Eleven.

Frank Sinatra as Danny Ocean in 1960’s Ocean’s Eleven.


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


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 black 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.

The black suit, tailored by the Rat Pack’s preferred tailor Sy Devore, is single-breasted with a subtle black overcheck to provide some self-contrast. The ventless jacket has notch lapels, jetted breast and hip pockets, and 3-button cuffs. It closes with a medium-to-high stance three-button front.

The suit trousers are single-pleated with cuffed bottoms that break high on his feet, clearly showing his black leather plain-toe bluchers and thin black dress socks.

“Please don’t take this out of context. It’s not what it looks like.” – Frank Sinatra, 1960

Although the look is similar both times – white shirt, solid tie – Sinatra dresses appropriately for the occasion both times.

When recruiting Vince and downing a highball or two at the burlesque club, Sinatra has his top two suit buttons fastened. As he also does this with his gray sportcoat, this could be Sinatra’s indication that he is going casual.

He 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 pointsfall outside the suit and drape over the lapels. When he needs to look good later on, Sinatra ensures that his collars stay in place.

kitchen CAPTION

Did You Know? The man in the white shirt, in the background, is Dave White, Sinatra’s long-time stand-in.

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.

we need a CAPTION

Even after a night out drinking, a barfight, and running, Sinatra’s suit and tie still look as good at the end of the night as they did when he started it. #TotalDraperMove

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

The black 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.

sinatra vegas CAPTION

Sammy Davis, Jr. should’ve complained about having to spend half the movie in a garbage man’s uniform while Sinatra got to wear suits like this.

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.

These men could be staring so solemnly at either:
a) The corpse of a fallen friend
b) An empty bottle of Scotch

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 is a small white and black check 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.

In the most ridiculous film disguise yet, Sinatra alters his appearance after the robbery by changing his cuff links. Makes Cary Grant's sunglasses in North by Northwest genius by comparison.

In the most ridiculous film disguise yet, Sinatra alters his appearance after the robbery by changing his cuff links, making Cary Grant’s sunglasses in North by Northwest genius by comparison.

With his fancier collar and tie, Sinatra foregoes the pocketsquare. 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.

Seriously? They couldn't even do a close up? The whole movie is about a TIMED robbery and we have no clue what the heist planner's watch looks like. Come on.

Seriously? They couldn’t even do a two second close up? The whole movie is about a TIMED robbery and we have no clue what the heist planner’s watch looks like. Come on.

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.

Merry Christmas.

Merry Christmas.

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

Frank smoked unfiltered Camels. So did your grandfather and so should you.

Frank smoked unfiltered Camels. So did your grandfather and so should you.

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-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 black 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 pocketsquare.

Sinatra in a casino just looks right, doesn't it?

Sinatra in a casino just looks right, doesn’t it?

His basic elements are:

  • 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 cuffed bottoms/turn-ups
  • White dress shirt with tab collar and double/French cuffs
  • Black textured silk necktie, or a narrow white & black small check patterned silk necktie
  • Rounded square black cuff links
  • Black leather plain-toe bluchers
  • 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…

Buy the movie.

The Quote

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

The best revenge is massive success.


  1. Pingback: Sinatra’s Orange Sweaters in Ocean’s Eleven | BAMF Style

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