Sinatra’s Gray Sportcoat in Ocean’s Eleven

65 years ago today, the city of Hoboken, NJ celebrated “Frank Sinatra Day” in which the star – at the height of his early fame – was welcomed and regaled in his hometown. In honor of the original “Frank Sinatra Day”, here is Sinatra 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

Beverly Hills, December 1959

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


Like the 2001 remake starring George Clooney and Brad Pitt, the original Ocean’s Eleven was essentially bout eleven guys that you’d want to hang out with having fun in Vegas while trying to rob a few million dollars and wearing sharp suits. The remake both complies with modern casino security and takes advantage of recent filmmaking techniques to show the men pulling off a slick heist.

In the original, released in 1960, the heist itself is far less technical as five guys in eveningwear walk into darkened count rooms, force casino employees to sing “Auld Lang Syne”, and leave within two minutes with eleven million dollars.

The scenes I will focus on take place just before the guys leave for Vegas. Sinatra has been palling around Beverly Hills with Dean Martin and Peter Lawford, getting some last minute details before meeting up with everyone at the home of a crooked millionaire to plan the job. (Hey, they did that in the remake too!)

In this sequence, Sinatra confronts ex-wife Angie Dickinson, confronts ex-girlfriend Adele (not the singer), and meets the ten other men to show them his extensive plan, which includes pulling a handkerchief out of his pocket that has the five casinos on it.

What’d He Wear?

Sinatra, like the other characters (save for Sammy Davis, Jr.), spends the majority of the film in various suits. For these scenes, he wears a distinctive gray specked sportcoat with unique notch lapels that appear to be stylistically borrowed from “Ike jackets” – the service coats worn by some U.S. Army officers during World War II. Eventually, these lapels would be seen on safari coats and leisure suits during the 1970s.

Although Sinatra probably just liked the jacket, it is interesting to note that his character was a World War II Sergeant in the 82nd Airborne and would have worn these lapels on an Ike coat. If anyone knows the name for these unique lapels, please let me know below.

Sinatra’s lapels compared to those on the Ike coat of an 82nd Airborne technical sergeant. Coincidence? I think yes, definitely yes. But interesting all the same.

The jacket, in addition to the lapels which I have already talked to death, is ventless with a 3-button front, 3-button cuffs, a welted breast pocket, and flapped hip pockets. In the breast pocket he wears a paisley pocket square in what looks like light gray silk with red accents. He wears the jacket buttoned, alternating between the top two and just the middle button. Like anyone else who was raised during the Golden Era of men not looking like goons, Sinatra never buttons all three buttons.

Even when you’ve been rejected by the only woman who could ever love you for the bum you are and are heading down to drink yourself dizzy in a hotel bar, keep the pocket square intact and the jacket buttoned.

Underneath the jacket, Frank wears a white shirt with barrel cuffs and a long-pointed spread collar. His tie is a very dark blue with a few blue pin dots.

Sinatra’s look is versatile: It works for both planning a multimillion dollar casino heist with ten Army buddies and breaking up with a leopard-print-wearing floozie who will throw an ashtray at you.

Finally, Frank pairs it all with a pair of black pleated slacks with cuffed bottoms. We hardly see the belt he wears, but if it matches his leather laced shoes, then it is a dark oxblood. His socks are also black.

Martin, Sinatra, and Lawford look as though they’ve just been told the house is out of booze.

Interestingly, Sinatra doesn’t wear a watch for most of the movie. He also has a pink ring that comes and goes. In this sequence, it is gone, so you’ll just have to wait with bated breath.

Go Big or Go Home

Sinatra’s attire here is an appropriate “weekend suit”. Not formal enough for a big meeting at work or a job interview, this would be the clothes of choice for dressing up on the weekend and looking just a little better than the guy next to you in a polo and slacks.

Luckily for us, Sinatra provides his own soundtrack.  This was filmed in 1959, the same year as his No One Cares album, and features some songs that would describe how Danny was feeling about his wife leaving him: “I Don’t Stand a Ghost of a Chance With You” and “Why Try to Change Me Now?” Of course, just listening to any Sinatra is a good decision anytime.

What to Imbibe

Everyone associates the Rat Pack with drinking and drinking hard. Ever since the 1940s, Sinatra had been a fan of Jack Daniel’s Tennessee Whiskey, saying it helped him sleep during various eras of heartbreak, 75% of which probably directly attributed to Ava Gardner. The whiskey became so linked to Sinatra that he was buried with a bottle of Jack Daniel’s and his usual unfiltered Camel cigarettes, both tucked into his funeral suit.

We don’t see any Jack Daniel’s during Ocean’s Eleven, but the guys still manage to get in plenty of drinking. Brands are also rarely seen, save for Dean Martin’s J&B and some blocked out bottles of Cutty Sark.

So, taking Sinatra’s preferred drink and taking into account the various Whiskey-and-Sodas he drinks throughout…

Jack & Soda

Uncomplicated and satisfying, a highball is the perfect drink for getting a refreshing taste of booze any time of day without getting hammered. They are also extremely easy to make. First, decide if you want ice or not. If you don’t, move on. Add the whiskey, in this case Jack Daniel’s. Again, this is all up to how you’re feeling – either a few drops, a shot, half the glass, or most of the glass. You’re Sinatra, so let’s at least go with half the glass. Then, get ahold of your soda siphon (which please tell me you have) and squirt in just as much as you need.

I’ve read exact recipes for highballs (ex: 2 oz. of liquor, 4 oz. of soda) but don’t see the point; pour as much as you want of whatever you want.

How to Get the Look

A woman is also part of Sinatra’s look. If you can get your hands on Angie Dickinson, especially the 1960 version of her, kudos.
Otherwise, any woman will do.

No need to be exact, but get the general essence. Sinatra dangerously teeters on the edge of a few faux pas (all the gray, brown, black, and blue clashing) but manages to pull it off. If you don’t think you can, carve out your own style.

  • Specked gray sportcoat with Ike-style notch lapels, 3-button front, welted breast pocket, flapped hip pockets, 3-button cuffs, and ventless back
  • White dress shirt with spread collar and buttoned barrel cuffs
  • Dark blue necktie with a few blue pin dots
  • Black pleated slacks with belt loops and cuffed bottoms
  • Dark oxblood leather belt
  • Dark oxblood leather laced shoes
  • Black dress socks
  • Light gray and red silk paisley pocket square

Do Yourself a Favor and…

Buy the movie.

The Quote

Listen to me very carefully, my dear. I picked you up at the Biltmore Bar because I thought you were attractive and I had nothing better to do. I made a pass at you for the very same reasons.


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