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
Let’s ease into #SinatraSaturday with a return to Pal Joey, the story of an ambitious nightclub performer played by Ol’ Blue Eyes himself who finds himself in a love triangle with an ingenue chorus girl (Kim Novak) and a wealthy widowed former stripper (Rita Hayworth), all set to more than a dozen classic Rodgers and Hart tunes.
This sequence finds Sinatra’s Joey Evans, firmly ensconced in the employ – and bedroom – of Hayworth’s Vera Prentice-Simpson, who is promising him his own club. The mesmerized Joey watches Kim Novak’s Linda perform “My Funny Valentine” (dubbed by Trudy Stevens), but Vera wants nothing to do with a rival for Joey’s affections and she forces the smitten lothario to fire his favorite singer.
Unable to actually fire her, Joey instead suggests to Linda that she take on “the strip” instead of her song, knowing that her pride will force her to quit. Linda sees right through it, despite Joey’s compelling arguments like…
You’re the best built mouse in the joint, so let’s take advantage of it.
What’d He Wear?
The scene begins with Sinatra in prime Sinatra: looking casual yet ultimately intentional with his hat tilted over one side of his face, his tie knotted but nonchalantly loosened, and his eyes focused.
Joey’s hat is the same black felt short-brimmed trilby with its four gold-corded band that Sinatra had worn in an earlier scene with his dove gray dinner jacket. The informal headgear is a more appropriate choice with this dressed-down outfit.
The light gray shirt is always worn with the top button undone, spreading the long point collar leafs out and leaving the neat Windsor knot of his gray grenadine silk tie to hang down an inch or so from the neck. The shirting has a silky sheen, suggestive of a high-twist cotton. The large square double (French) cuffs are fastened with a set of large, round ridged silver cuff links.
The shirt’s most individualistic detail? “Joey” monogrammed in large blue-gray cursive stitching on the left breast pocket.
Joey wears dark gray flannel trousers, a traditional accompaniment for the navy blazer though khakis have emerged as a sporty, summer-friendly alternative in recent decades. The trousers have a long rise to Sinatra’s natural waist, where they are held up with a black leather belt with a brass single-prong buckle.
The double reverse-pleated trousers have “quarter top” slanted side pockets, jetted back pockets that each close with a button, and are finished with turn-ups (cuffs) on the bottoms.
Once his dirty work is done for the day, Joey dons his jacket, a vivid navy blue serge single-breasted blazer with three shining gold crested shank buttons to match the three buttons on each cuff. Joey wears a white linen pocket square neatly folded in the welted breast pocket, and the two flapped pockets are placed low on his hips, straight in line with the lowest blazer button. The blazer also has double vents.
When Vera arrives home, asking Joey to leave before her “decent” dinner guests arrive, he’s kicking back on her couch, still wearing his blazer and his black calf leather derby shoes. His socks are worn with black socks.
Barely seen on his left wrist is the black leather strap of Joey’s gold tank watch, likely an item that belonged to Sinatra himself.
What to Imbibe
If you’re Frank Sinatra, the drink is simple: two fingers of Jack Daniel’s over three ice cubes, topped off with a splash of water. Of course, if you’re looking get creative and combustible yet classic with your spirits, consider the Blue Blazer, brought to us by “father of American mixology” Jerry Thomas. Just be cautious to avoid anything excessively flammable during its creation.
As recounted by David Wondrich in his seminal tome Imbibe!, Jerry Thomas claimed to have invented the world’s first recorded “flaming cocktail”, the Blue Blazer, which started appearing in drinking holes in the years leading up to the Civil War. Whether or not Thomas was the actual inventor, it was his recipe that first appeared in print in Thomas’ 1862 bartenders’ guide How to Mix Drinks, with the simple enough ingredients of Scotch whisky and boiling water, then calling for its maker to:
Add one wineglass of boiling water, then set it on fire, and while blazing, pour from each into the other mug, being particular to keep the other blazing during the pouring process. Serve in small bar tumblers. Add piece of lemon skin, pour mixture into glass blazing, and cover with cup.
Thomas himself was reportedly a master of artfully hurling the flaming Scotch-and-water mixture back and forth between two silver mugs, though Thomas drolly noted that “the novice in mixing this beverage should be careful not to scald himself.”
Perhaps it’s better to stick to Frank’s tried-and-true Jack Daniel’s and water after all.
How to Get the Look
The navy blazer is a timeless menswear piece just as effective now as it was sixty years ago when Frank Sinatra donned one as a successful playboy crooner in Pal Joey. As the titular Joey, Ol’ Blue Eyes added a personal touch to this traditional staple with a monogrammed shirt, bold cuff links, and one of the singer’s signature hats.
- Navy serge single-breasted blazer with 3 gold shank buttons, with welted breast pocket, straight flapped hip pockets, 3-button cuffs, and double vents
- Light gray high-twist cotton shirt with long point collar, plain front, monogrammed breast pocket, and double/French cuffs
- Silver ridged round cuff links
- Gray grenadine silk tie
- Dark gray flannel double reverse-pleated high-rise trousers with belt loops, slanted side pockets, button-through jetted back pockets, and turn-ups/cuffs
- Black leather belt with brass single-prong buckle
- Black calf leather derby shoes
- Black socks
- Black felt short-brimmed trilby with gold 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.
The only thing I’m superstitious about is 13 in a bed.