Sinatra’s Dark Gray Ocean’s Eleven Suit

Today marks the sad anniversary of 15 years since the death of the legendary Frank Sinatra. To pay tribute to the man, here is another installment from the original Ocean’s Eleven.

Frank Sinatra as Danny Ocean in the original Ocean's Eleven.

Frank Sinatra as Danny Ocean in the original Ocean’s Eleven (1960).


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


A great suit is great not just only for looking good but also for its versatility. In several key scenes in Ocean’s Eleven, Sinatra wears a sharp gray suit, the same suit seen in the iconic Rat Pack poster of all five members standing in front of a sign for the Sands in Vegas. What makes this suit diverse is that Sinatra’s character, Danny Ocean, wears it for both a night at the casino and the funeral of an old buddy.

In an interesting reversal, the original Ocean’s Eleven is actually darker than the modern remake. According to Frank Sinatra, Jr., in the DVD commentary, Danny and his men were to charter a plane, flown by one of the “eleven”, and get the stolen money out of Vegas successfully. Unfortunately, the entire group would then be killed in a plane crash.

Other than the irony, there’s not really much that is very funny about this ending. After it was decided that no one really cared for it, an alternate ending was developed. The new ending still featured death, but only one compared to eleven. This sort of black comedy was not very common in 1960, and the Rat Pack handled it perfectly. They would be the perfect guys to defy cinematic conventions and say, “Fuck it. Someone’s gotta die for this movie.”

What’d He Wear?

Sinatra wears a dark gray wool suit, tailored for him by the legendary Sy Devore.

According to a 2001 Los Angeles Times article posted on, Sinatra ordered all of his suits from Devore with 2.25″ wide lapels, and the notch lapels on this suit’s single-breasted jacket are no exception. The ventless jacket has three buttons in the front with a medium stance as well as a welted breast pocket, jetted hip pockets, and three decorative cuff buttons on each sleeve.

The single-pleated trousers have a high rise and plain-hemmed bottoms with no turn-ups or cuffs. There are side pockets, which Sinatra uses mostly for his hands. Danny wears a thin black leather belt with a squared brass clasp for Bergdorf’s funeral.


The suit is worn simply for Danny’s casual night of recon in the casino, with a casual white shirt and black tie. This simple look may be utilitarian for Danny, who is trying not to be recognized despite a run-in with Red Skelton and his ex-girlfriend Adele.

Last week, I focused on George Clooney's slick casino entrance as Danny in the 2001 Ocean's Eleven. In 1960, Sinatra showed that sometimes there's not much cooler than just an understated but direct walk from door to slots.

Last week, I focused on George Clooney’s slick casino entrance as Danny in the 2001 Ocean’s Eleven.
In 1960, Sinatra showed that sometimes there’s not much cooler than just an understated but direct walk from door to slots.

The shirt is a soft white cotton with buttoned barrel cuffs. It also features a long, American-style button-down collar. The shirt buttons down a front placket, with white buttons to match those on the collar and cuffs.

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Danny skimps on accessories, wearing only a solid black necktie and no handkerchief or jewelry. He wears the suit with black leather shoes and black socks.

For the film’s finale, the funeral of Danny’s war pal Tony, Danny wears a dressier shirt, a white button-down with double cuffs. The tab collar is fastened with a gold collar pin, worn with a thin dark navy silk necktie.

As opposed to his night in the casino, Danny wears more accessories at the funeral. Since he is now wearing a shirt with French cuffs, Danny sports a set of rounded square onyx cuff links. In his breast pocket, he wears a yellow paisley silk display handkerchief with blue accents.


Sinatra manages to look totally composed no matter what situation he’s in.

The pocket square might be a little loud for a funeral, but the film’s tone makes it appropriate.

Go Big or Go Home

Despite being the leader of a multi-million dollar-stealing criminal gang, Danny Ocean is still a laidback, casual guy. He has a girlfriend in every city and, when running into an ex, smoothly slips his hotel key down her dress. Okay, this might be a bit of early-60s misogyny, but it looks cool on screen. Until she calls his ex-wife and tosses the key into a plant.

Still, he keeps his calm. He drinks Scotch and soda while making arrangements for his friend’s funeral, from a mini-bar kept on the table in his hotel room that consists of the essentials: whiskey, vodka, and a bottle of seltzer.

The funeral of a friend is never easy. Be sure to honor his memory with enough whiskey-and-sodas (Whiskies-and-soda? Whiskies-and-sodas?) to float the Titanic.

The funeral of a friend is never easy. Be sure to honor his memory with enough whiskey-and-sodas (Whiskies-and-soda? Whiskies-and-sodas?) to float the Titanic.

If we should learn anything from Danny Ocean, it should be one easy philosophy: Take it easy and have a drink.

How to Get the Look

Sinatra shows off a couple of ways to diversify the suit, either worn simply and casually or with more colorful accents. While Sinatra chooses simple for the casino and loud for the funeral, you may find yourself having better luck switching that formula.

Sinatra being Sinatra.

Sinatra being Sinatra.

  • Dark gray wool custom-tailored Sy Devore suit, consisting of:
    • Single-breasted 3-button jacket with notch lapels, welted breast pocket, straight jetted hip pockets, 3-button cuffs, and a ventless rear
    • Single-pleated high rise trousers with belt loops, side pockets, and plain-hemmed bottoms
  • White dress shirt, either with button-down collar and button cuffs or tab collar and double/French cuffs (with a gold collar pin and rounded square onyx cuff links)
  • Solid dark silk necktie, either black or navy
  • Thin black leather belt with a brass squared clasp
  • Black leather shoes
  • Black dress socks

Do Yourself a Favor and…

Check out the movie.

I’m feeling particularly literary lately. For a great firsthand account of life with Sinatra, pick up Mr. S, the memoir penned by George Jacobs, Sinatra’s valet from 1953 to 1968. Jacobs, who saw various ups and lows in Sinatra’s life, shines a new light on the man as well as his contemporaries and acquaintances, such as JFK and his father, Dean Martin, Marilyn Monroe, Mia Farrow, mobster Sam Giancana, and – of course – Ava Gardner.


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