Frank Sinatra, multi-talented entertainer facing retirement
Los Angeles, Summer 1971
Series: Sinatra: All or Nothing At All
Air Date: April 5-6, 2015
Director: Alex Gibney
Born December 12, 1915, Frank Sinatra had recently turned 55 when he started talking seriously with close friends about retirement. For more than 30 years, the entertainer had enjoyed a landmark career, beginning with his days as a pop idol, then a career downturn in the early ’50s that was reinvigorated by an Oscar win for From Here to Eternity and a series of concept albums for Capitol Records that launched him to massive success.
Throughout the ’60s, Sinatra evolved from one of the most popular entertainers in the nation to one of the most influential entertainers across the world. He had founded his own record label with Reprise Records, been a confidante of a sitting U.S. President (before their famous falling-out), and continued to prove his success on the charts with songs like “My Way” (despite his resentment for this particular tune.)
Like so many successful 55-year-old Americans, Ol’ Blue Eyes decided to hang up his tilted hat and retire, with his final performance to be June 13, 1971, at the Ahmanson Theatre in Los Angeles. Alex Gibney’s 2015 HBO documentary Sinatra: All or Nothing at All was framed around the singer’s hand-chosen setlist for the concert, and how the eleven musical milestones Sinatra selected essentially told the story of his life to that point.
(Of course, Sinatra’s “retirement” was short-lived and he would be back in the recording studio within two years, never ceasing to work until his death in May 1998 at the age of 82.)
What’d He Wear?
“For me, a tuxedo is a way of life,” Sinatra once stated, according to Bill Zehme’s The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’. “The costume empowered them, enlarged them,” Zehme writes of FS and his Rat Pack pallies, who regularly took the stage in black or midnight blue dinner suits, eschewing less formal lounge suits and particularly daytime colors like gray or brown.
Perhaps representative of Sinatra’s struggle between maintaining his classic repertoire and appealing to new audiences, his black tie kit for the 1971 farewell concert blends the emerging fashion trends of the ’70s with his time-tested philosophy toward evening dress.
Through the ’60s, Sinatra was a customer of Beverly Hills tailor Sy Devore, who also catered to his stylish singing pals like Dean Martin, Sammy Davis Jr., and Elvis Presley, though Devore’s death and Sinatra’s ascension to his “Chairman of the Board” reputation led to his taking his business to more conservative clothiers like Brooks Brothers, Carroll & Co., and Dunhill, before ultimately heading across the pond and into shops of reputable British cutters like Cyril Castle.
Made from a high-quality midnight-blue wool, the single-breasted dinner jacket has an elegant black silk-faced shawl collar that rolls to a single black plastic 2-hole sew-through button at a position that coordinates with the then-fashionably lower rise of trouser waistbands. The single vent and the flaps over the hip pockets belong more on a business suit or lounge suit than a dinner jacket. Sinatra dresses his welted breast pocket with a subdued white folded linen pocket square, rather than one of his more colorful kerchiefs in red or his favorite color, orange. The straight, wide shoulders build up the singer’s famously lean physique, roped at the sleeveheads and finished with two plastic buttons on each cuff.
“He never wore a cummerbund, always a cinched-up vest,” observed Zehme. His black formal waistcoat can be glimpsed following the low-fastening lines of his dinner jacket during the 1971 concert, only seen in greater detail in behind-the-scenes photography of Sinatra in his dressing room before the concert. Stripped of his jacket, we see the black backless waistcoat, essentially two silk panels that flare down each side of the torso, fastened behind the back of the neck and around the back of his waist with an ornamental button-closure in the front that would be covered by the buttoned dinner jacket.
“My basic rules are to have shirt cuffs extended half an inch from the jacket sleeves,” Sinatra explained. Unlike Dino, who favored casual button-down shirts even with his tuxedoes, FS invariably sported traditional white cotton evening shirts meant to be worn with black tie. Sinatra’s shirts were detailed with pleated bibs, which ranged from frilly pleats as found on his shirts through the ’50s as seen in Pal Joey and when accepting his Oscar to more irregular diagonal pleats made for him by Nat Wise of London (now Anto Beverly Hills) in the ’80s.
This 1971 evening shirt has more traditional narrow pleats and a long point collar that appears to be the shirt’s only concession to the era’s trends. The double (French) cuffs emerge neatly from the ends of his sleeves, showing just a flash of the mother-of-pearl cuff links that echo the pearl-esque shine of three clear plastic buttons up the front placket of the shirt.
The massive wings of Sinatra’s black satin silk bow tie date it the most to the early ’70s, proportionally compatible with the shirt’s large collar but dwarfing the more moderate width of the jacket’s lapels.
“Trousers should break just above the shoe,” Sinatra prescribed, adding the guidance that the wearer should “try not to sit down because it wrinkles the pants. If you have to sit, don’t cross your legs.” The entertainer follows his own advice, gently perching himself on a stool but never outwardly sitting, thus maintaining the integrity of his matching midnight-blue dinner suit trousers, detailed with the signature black silk stripe down the side of each leg.
The plain-hemmed trouser bottoms cover the tops of his black patent leather kicks, which appear to be inside-zip boots rather than his signature slip-on pumps with straight grosgrain bows. The boots are a surprising concession to early ’70s fashion for a sartorial traditionalist like Sinatra, but they retain his preferred gleam.
“Shine your mary janes on the underside of a couch cushion,” Sinatra also advised, which his road manager Tony Oppedisano explained was the singer’s actual practice before heading on stage. “You know why he did that? When he was a kid, he’d do it at home and his mother would smack him. He knew nobody else was ever gonna smack him for it.”
Sinatra keeps his jewelry and accessories to a minimum, with only his usual gold signet ring shining from his left pinky. Zehme writes that this ring “bore the ancient Sinatra family crest, forged in the old country, a crowned griffin with shield.”
What to Imbibe
Frank Sinatra’s preference for Jack Daniel’s Tennessee whiskey has been so mythologized that the brand has even marketed a special “Sinatra Select” bottling. However, on the night of his prospective swan song in L.A., Thomas Thompson reported for LIFE:
He was making small talk and a frog crept into his voice. Someone noticed it. “You want something to drink, Frank?” There is always someone there to fetch for him. “Yeah… thanks… I’d like a vodka.” The man started out. Frank stopped him. “Either that or a cup of hot tea.” The man hurried away. Frank stopped him once more. “Better get booze. Forget the tea.”
Thompson later reports that, after the vodka arrived, “Frank squeezed half a lemon into it and took a long drink.” Zehme recounted the story in The Way You Wear Your Hat, contextualizing that Stolichnaya was Sinatra’s vodka of choice, always enjoyed on the rocks unless it was the driving spirit of a very dry martini. Given that the Chairman didn’t throw the drink back in his face, the nameless gofer from Thompson’s article likely poured the correct Stoli.
How to Get the Look
Frank Sinatra cycled through tuxedoes of varying style, color, cloth, and detailing throughout more than a half-century of superstardom, though the most enduring look remains the dark shawl-collar dinner jacket, which could be appointed to suit the contemporary trends as seen when Ol’ Blue Eyes wore it with a wide-winged bow tie and patent leather boots for his farewell concert in 1971.
- Midnight-blue wool single-button dinner jacket with silk-faced shawl collar, welted breast pocket, straight flapped hip pockets, 2-button cuffs, and single vent
- White cotton evening shirt with large point collar, narrow-pleated bib (with mother-of-pearl studs), and double/French cuffs (with mother-of-pearl cuff links)
- Black satin silk oversized butterfly-shaped bow tie
- Black silk low-fastening backless formal waistcoat
- Midnight-blue wool flat front formal trousers with black silk side stripes and plain-hemmed bottoms
- Black patent leather inside-zip ankle boots
- Black silk dress socks
- White linen pocket square
- Gold signet pinky ring
Do Yourself a Favor and…
Check out the two-part HBO documentary, available on DVD and currently streaming on Netflix.
Having been a saloon singer all my life, I’ve become an expert on saloon songs: the kind of things that cause men to cry in their beers.