Pal Joey: Sinatra’s Gray Dinner Jacket

Frank Sinatra as Joey Evans in Pal Joey (1957)

Frank Sinatra as Joey Evans in Pal Joey (1957)


Frank Sinatra as Joey Evans, womanizing nightclub singer

San Francisco, Spring 1957

Film: Pal Joey
Release Date: October 25, 1957
Director: George Sidney
Costume Designer: Jean Louis


Today marks the birth of Frank Sinatra, the Chairman of the Board himself, born on December 12, 1915, in Hoboken. This son of tenement-dwelling Italian immigrants grew to be one of the most influential, best-selling music artists in history.

Sixty years ago, Sinatra was rising as one of the biggest stars in the world when he starred as the titular Pal Joey, a performance that earned him a Golden Globe award. Originally a stage musical starring Gene Kelly as the singing and dancing anti-hero, Pal Joey was reconfigured for the screen with the character more reflective of Sinatra’s own charming yet mischievous “nice guy” persona.

Though he played the title character, Frank Sinatra reportedly insisted upon co-star Rita Hayworth receiving top billing because “For years, she was Columbia Pictures,” although he’s also credited with the more laconic explanation of simply saying, “Ladies first.”

The film also starred Kim Novak as ingenue chorus girl Linda English, and Sinatra remarked of being billed between the two of them that, “That’s a sandwich I don’t mind being stuck in the middle of.”

Frank Sinatra and Kim Novak in Pal Joey.

Frank Sinatra and Kim Novak in Pal Joey.

Despite actually being three years younger than Sinatra, Rita Hayworth plays the cougar-ish Vera Prentice-Simpson, a former burlesque performer who takes on the younger Joey Evans  as her “boy toy” in return for financing his dreams of owning a nightclub. In his 2008 book Sinatra in Hollywood, author Tom Santopietro declared the scene in which Sinatra sings his own classic standard “The Lady is a Tramp” to Hayworth as the finest moment of Ol’ Blue Eyes’ film career.

I received a request from BAMF Style reader Mark earlier this year to showcase Frank Sinatra’s style in Pal Joey, so it seemed apt to start by featuring this scene on the chairman’s actual birthday. Happy birthday, Frank!

What’d He Wear?

As a professional entertainer, Frank Sinatra’s titular Joey spends much of the film in variations of formal attire from sharp dinner suits in midnight blue and black mohair (at the beginning and end, respectively) as well as a red flecked mess jacket when on the bandstand and a white tie and tails ensemble during a fantasy sequence in the musical finale.

After the club where Joey is performing receives a surprise visit from the glamorous and powerful ex-burlesque performer Vera Prentice-Simpson, Joey emerges from the back room to serenade her in an equally impromptu rendition of “The Lady is a Tramp,” dressed in a non-traditional black tie kit consisting of a dove gray shawl-collar dinner jacket with a lace-trim pleated front shirt and midnight formal trousers.

Joey closes out a show-stopping number for Vera's benefit. Note that the rest of the band still wears red mess jackets.

Joey closes out a show-stopping number for Vera’s benefit. Note that the rest of the band still wears red mess jackets.

The gray dinner jacket has self-faced shawl lapels of a classic width that neatly roll to a single button positioned perfectly at the waist line for harmonious lines with only the shirt visible above the buttoning point and only the trousers below it.

Jetted, rather than flapped, pockets on the hips continue the clean lines of the ensemble and are considered more appropriate for formal wear and dinner jackets. Joey wears a white linen pocket square neatly folded into the welted breast pocket. There are three buttons on each cuff and, per dinner jacket tradition, there are no vents.


Joey wears a white pleated-front dinner shirt in cotton voile with a black silk butterfly-shaped bow tie. The shirt’s squared double (French) cuffs are held together with the same large silver-toned ridged disc links as he wears elsewhere.

Joey and his canine pal prepare for his evening's performance in his dressing room.

Joey and his canine pal prepare for his evening’s performance in his dressing room.

The Rat Pack had many of their shirts made from Nat Wise of Beverly Hills, which was adapted into Anto Shirt in 1987, and this unique shirt is likely no exception, though it predates Frank’s association with Dean Martin and Sammy Davis Jr.

The subtle lace trim on the shirt’s pleated front looks like it was constructed from ripped strips of paper, delivering just the needed level of insouciant imperfection befitting the character’s swagger. The pleats are a bit affected but hardly as flashy as the ruffled front of James Bond’s tuxedo shirt in On Her Majesty’s Secret Service. The shirt has a standard placket with mother-of-pearl buttons.

Sinatra doing what he does best.

Sinatra doing what he does best.

In accordance with this less formal ensemble, Joey doesn’t wear the traditional waist covering (cummerbund or waistcoat) that often accompanies black tie. He wears white fabric suspenders (braces) with gold adjusters with white leather hooks that connect to two double sets of buttons along in the inside of the front trouser waistband and a single set of two buttons on the outside of the back trouser waistband, split by a narrow “fishmouth” notch that adds flexibility as Joey moves or sits.

Joey catches Linda's eye through the barred window of his dressing room.

Joey catches Linda’s eye through the barred window of his dressing room.

Joey’s formal trousers are midnight blue, possibly the trousers from his dinner suit at the beginning of the movie, with double reverse pleats and a satin side stripe that extends from the plain-hemmed bottoms up to the top of the waistband. They have no back pockets but straight pockets along the side seams, behind the satin braids, where Sinatra often places his hands.


Production photo of co-stars Frank Sinatra and Barbara Nichols in Pal Joey (1957)

Production photo of Frank Sinatra with Barbara Nichols, yet another of the beautiful women with whom he co-starred in Pal Joey (1957). Nichols was a mainstay of late 1950s productions that called for brassy blonde bombshells from Sweet Smell of Success (1957) and Where the Boys Are (1960) to the first episode of The Untouchables in 1959.

Black oxfords are considered the most formal lace-up shoe that one can wear with black tie, although Sinatra was certainly known to wear the uber-formal opera pumps with some of his tuxedos… such as this pair of John Lobbs worn with this custom Cyril Castle dinner suit in the 1970s.

But back to Pal Joey, where Sinatra wears a more practical and accessible pair of black patent leather cap-toe oxfords with black silk dress socks.

“A hat’s not a hat till it’s tilted,” sang Sinatra with Dean Martin and Bing Crosby in “Style” for Robin and the 7 Hoods (1964), and Sinatra’s ability to effectively wear a hat has become part of his lore.

Naturally, Joey thus tops of his look with his black corded-band trilby when heading out of the club with Vera on his arm.

The hat is less formal than the homburgs suggested as appropriate headgear with black tie, but his less-than-formal dinner jacket excuses it. The black felt hat has a pinched crown with a band consisting of four thin tan cords joined together on the left side.

This Pal Joey hat was undoubtedly made by Cavanagh, whose hats Sinatra wore exclusively in real life, though I can’t find more information about this hat specifically.

Joey takes in his surroundings.

Joey takes in his surroundings.

Joey wears a watch on his left wrist that isn’t clearly seen anywhere on screen, though it appears to be a gold tank watch on a black leather strap, an elegantly simple style appropriate for black tie and befitting Sinatra’s own image.

Joey shares drinks and dreams with Vera while tending bar on her yacht.

Joey shares drinks and dreams with Vera while tending bar on her yacht.

One of Pal Joey‘s four nominations at that year’s Academy Awards was for Best Costume Design, appropriately recognizing the achievements of Paris-born designer Jean Louis.

How to Get the Look

Frank Sinatra’s signature look on stage was a dark tuxedo with a red silk pocket square, so it’s a treat to see the Chairman take on this non-traditional yet beautifully tailored dinner jacket in Pal Joey.

  • Dove gray shawl-collar single-button dinner jacket with welted breast pocket, straight jetted hip pockets, 3-button cuffs, and ventless back
    • White linen pocket square, folded in breast pocket
  • White cotton voile dinner shirt with point collar, lace-trimmed pleated front, and squared double/French cuffs
    • Round silver ridged cuff links
  • Black satin silk butterfly-shaped bow tie
  • Midnight blue double reverse-pleated formal trousers with satin side stripes, straight/on-seam side pockets, fishmouth-notched back waistband with two suspender buttons, and plain-hemmed bottoms
  • White suspenders/braces with gold adjusters and white hooks
  • Black patent leather cap-toe oxford shoes
  • Black silk socks
  • Black felt short-brimmed fedora with tan quadruple-corded band
  • Gold tank watch on black leather strap

Do Yourself a Favor and…

Check out the movie, and read up on your Sinatra style. Several years ago, I was honored to receive the gift of Bill Zehme’s The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’, a definitive bible of Ol’ Blue Eyes’ approach to sartorialism and life, from BAMF Style reader Teeritz.

I have also heard good things about a newly released book, Eliot Weisman’s The Way It Was: My Life with Frank Sinatra, which explores the last two decades of Sinatra’s life.

The Quote

I got it figured out. You treat a dame like a lady, and you treat a lady like a dame.


  1. Wolf

    Whilst never usual, grey summer dinner jackets had been a thing in the 1930s. Alternatives to the still new white Dinner jacket included ‘Burma Tan’ and a very light grey – rather like this one.

  2. Mark Gibson

    First rate coverage of Sinatra at his best. He turned a bitter spiteful lyric into a sexy, beautiful showstopper. The man who wrote the book on film BAMFery. Famed for his elegance and respect for his fans, even before anyone thought he’d amount to anything. I once heard he initially turned down PAL JOEY and said it should go to Gene Kelly. Then the studio talked about getting Billy Wilder to direct it as a non-musical drama with Marlon Brando as Joey. Sinatra saw that as the dog’s breakfast it would have been and suddenly became available. A great summer formal outfit for a man who’ll do anything to get to the top.

  3. Pingback: Pal Joey: Sinatra’s Navy Blazer | BAMF Style
  4. Pingback: Frank Sinatra's 1971 Retirement Concert Tuxedo » BAMF Style

Leave a Reply