Pal Joey: Sinatra’s Silk Loungewear

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


The same year that Pal Joey was released, Frank Sinatra released A Swingin’ Affair!, his latest concept album from Capitol Records. The fourth track, “I Guess I’ll Have to Change My Plan”, was written by Arthur Schwartz and Howard Dietz in 1929, when it was introduced by Clifton Webb in the songwriting duo’s revue The Little Show.

I guess I’ll have to change my plan
I should have realized there’d be another man
Why did I buy those blue pajamas
Before the big affair began

For decades, the song carried the subtitle “The Blue Pajama Song” for the above lyric (which Julie London changed to “black pajamas” in her 1959 rendition) and became a standard for vocalists like Tony Bennett, Bing Crosby, Bobby Darin, Patti Page, Rudy Vallee, and most recently Bob Dylan on his recent album, Triplicate, which included many numbers from the “Great American Songbook”.

This #SinatraSaturday, let’s take a look at the luxurious silk blue (and red) pajamas that Ol’ Blue Eyes wore for a brief but memorable scene in the 1957 Technicolor musical Pal Joey.

What’d He Wear?

Forced out of the house for the night when his girlfriend Vera (Rita Hayworth) hosts a sophisticated soiree, Joey Evans retreats to Vera’s opulent yacht where he plans to spend the evening in luxurious leisure, chain-smoking Chesterfields and reading the latest entertainment scoop from Variety, identified as the April 17, 1957 by its characteristically pun-tastic headline: TV sugar-‘codes’ old features.

Joey dresses for his hedonistic night in with a rakish red paisley-on-midnight blue silk brocade suit that consists of a sash-tied smoking jacket top and matching tuxedo-inspired pajama bottoms.

The good life, à la Joey Evans.

The good life, à la Joey Evans.

The fabulous fifites were the last stand of the smoking jacket, a bridge between casual comfort and formal fashion that Sir Hardy Amies addressed in his strict 1964 manifesto ABC of Men’s Fashion as “as old fashioned as a smoking room… yet the idea is charming and very sensible.”

With its tailored hip-length fit, shawl collar, padded shoulders, and ventless back, Joey’s top qualifies as a traditional smoking jacket. The wide shawl collar and turnback cuffs appear to be black velvet with red silk trim. It ties in the front with a sash made from the same red-on-blue paisley fabric as the rest of the outfit, and it has hip pockets and a welted breast pocket where Joey wears an off-white silk pocket square that matches his cream silk cravat.

Joey's night of solitude is complicated by the surprise arrival of his former girlfriend Linda English (Kim Novak).

Joey’s night of solitude is complicated by the surprise arrival of his former girlfriend Linda English (Kim Novak).

Like the smoking jacket-inspired top that borrowed styling cues from a shawl-collar dinner jacket, the pajama pants are similar to tuxedo trousers with their red silk side braiding that echoes the piping on the lapels and cuffs.


The only truly appropriate footwear for an outfit like this would be personalized velvet slippers, and Joey absolutely rises to the occasion. Velvet slippers remain a mainstay of classic menswear outfitters like Brooks Brothers, who currently offers them in black, dark green, and burgundy for $298 a pair. “Grandest of all are velvet slippers, with your monogram or crest embroidered in gold thread,” explained Amies when comparing the variety of slippers available to gents circa 1964.

Pal Joey recognizes the importance of the character’s vanity, beginning the scene with a shot of his black velvet slippers with their black leather trim, hard leather soles, and “Joey” emblazoned with red embroidery across each slipper, echoing the personalization on the shirt Joey wore earlier that day. He wears them with midnight blue ribbed silk dress socks.

Joey leaves no doubt regarding the ownership of his velvet slippers.

Joey leaves no doubt regarding the ownership of his velvet slippers.

On his left wrist, Joey wears the gold tank watch on a black leather strap that he wears throughout the film, likely an item that belonged to Sinatra in real life.


If you have any interest in seeing what the real Sinatra slept in, The Golden Closet currently features a plain beige pajama set that the entertainer wore in the late ’70s and gifted to his friend and personal costumer Michael Castellano. These pajamas are much more modest than the lavish loungewear that Joey Evans wore.

How to Get the Look

Frank Sinatra as Joey Evans in Pal Joey (1957)

Frank Sinatra as Joey Evans in Pal Joey (1957)

“Joey’s attempt at sophistication – donning a smoking jacket and monogrammed slippers – ensures he remains no more than a gigolo,” states Karen McNally in her thoughtful article for The Conversation about how Frank Sinatra’s films addressed postwar masculinity.

Joey Evans dressing in head-to-toe silk and velvet may not make him a gentleman… but it certainly makes him comfortable.

  • Red paisley-on-midnight blue silk brocade pajama suit:
    • Sash-tied smoking jacket with red-trimmed black velvet shawl collar and cuffs, padded shoulders, and ventless back
    • Trousers with red silk side braiding and plain-hemmed bottoms
  • Cream silk cravat
  • Cream silk pocket square
  • Black velvet slippers with black leather trim and red embroidered monogram
  • Midnight blue ribbed silk dress socks
  • Gold tank watch on black leather strap

Do Yourself a Favor and…

Check out the movie, and give Sinatra’s A Swingin’ Affair! album a swingin’ listen.

One comment

  1. MarkG.

    This is what I call a leisure suit! Reminds me of the outfits suave men like William Powell and Maurice Chevalier donned in ’30’s films. This “pint size Romeo” (as Vera calls him) really styles up to warrant a berth on Vera’s swanky yacht. Usually I don’t care for monogrammed items but they’re exactly right for the Joey brand. Some of Joey’s choices seem to be inspired by mega-rich yachtsman and playboy Gianni Agnelli. I’m going to get a look like this very soon. The yacht will take a little longer.

Leave a Reply