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.

Vitals

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

Background

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 evening wear walk into darkened count rooms, force casino employees to sing “Auld Lang Syne”, and leave within two minutes with eleven million dollars. Of course, the heist still requires some level of planning as Sinatra pals around Beverly Hills with Dean Martin and Peter Lawford, organizing some last minute details before meeting up with everyone at the home of a shady 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 gray flecked flannel sport jacket with distinctive 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. As an evolution of the 1940s “loafer jacket”, 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.

The ventless jacket has a three-button front, which he typically wears with the top two buttons fastened, as well as three-button cuffs and flapped breast pockets. He wears a gray-and-red paisley pocket square in the welted breast pocket.

Underneath the jacket, Frank wears a white shirt with rounded single-button barrel cuffs and a long point collar. His dark navy tie is patterned with blue pin dots.

Finally, Frank pairs it all with a pair of black pleated trousers with cuffed bottoms. He wears a black leather belt that coordinates with his black loafers and black dress socks.

Interestingly, Sinatra doesn’t wear a watch for most of the movie. He also has a pinkie ring that comes and goes, though it tends not to appear for this sequence.

Go Big or Go Home

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

Sinatra adopts a comfortable, casual, and ultimately distinctive look for his role as the former commando group’s organizer.

• Gray flecked flannel single-breasted 3-button sport jacket with Ike-style notch lapels, welted breast pocket, flapped hip pockets, 3-button cuffs, and ventless back
• White dress shirt with spread collar and buttoned barrel cuffs
• Navy pindot-patterned tie
• Black pleated trousers with turn-ups (cuffs)
• Black leather belt
• Black leather loafers
• Black dress socks
• Light gray and red silk paisley pocket square

Do Yourself a Favor and…

Check out 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.