The critic John Lahr put his finger on the salient points of Sinatra’s appeal in the 1950s: “His style – the thin, sensitive line of his look and of his singing – had the immanence of the hip combined with the articulateness of the traditional – The cocked hat, the open collar, the backward glance with the raincoat slung over the shoulder, the body leaning back with arms wide open in song …”. The clothes tell the story. On March 25, 1954 Sinatra won a “Best Supporting Actor Award” at The Academy Awards for his portrayal of Angelo Maggio in the film From Here to Eternity. He bounded onto the stage that evening wearing a slim, sleek black mohair tuxedo and a large grin. It was a new look. The kid stuff was over. From now on it was going to be The Big Room in New York, Las Vegas, and L.A.. To celebrate, he recorded a new version of “I’ve Got the World on a String”.
Sinatra’s new look was pared-down, laser-sharp. The style was part L.A. casual and part New York urbane, with some Vegas lounge hip and European Continental chic thrown in. Minimalist and iridescent, debonair, smooth, and polished, it was a look of complete confidence for a guy who had arrived at the grown-up table and intended to sit at the head of it. Sinatra and his pal Dean Martin set the tone for countless young men of the period who wanted to be as successful, cosmopolitan, and enjoy life as much as they appeared to. There are thousands of photos of the two of them over the decade, but the one I like best is from a trip they made together to London in 1961, at the apex of their popularity.
They were photographed at Heathrow Airport strolling towards Sinatra’s private jet on the tarmac, perfectly turned out in lightweight worsteds of pristine cut and fancy silk linings. The suits are trim: slightly close shoulder line, narrow lapels, slimming trousers. But consider the details, which always separate the men from the boys: both are wearing immaculate white dress shirts with French cuffs, and light silk foulards; straw fedoras with wide puggaree bands; and silk paisley pocket squares. Martin is sporting dressy Chelsea boots and Sinatra is shod in evening patent-leather pumps with bows. It was a flair interpreted best by Hollywood tailor and haberdasher Sy Devore (who died in 1966).
The Look could be seen on stage at The Sands Hotel in Vegas or the Copacabana in Manhattan, and is wonderfully captured in the 1960 film Ocean’s Eleven, Sinatra’s professional home movie starring himself and his pals – Peter Lawford, Martin, Sammy Davis Jr., Joey Bishop, and a handful of secondary players – pretty much dressed in the sort of outfits they normally wore on stage and off. Frank and Dean set the style for the group: accessories included long rolled button downs and pin collars always worn with French cuffs and good cuff links, neat woven silk ties and colorful paisley pocket squares (Frank preferred orange ones), tassel slip-ons, jaunty tilted felt and straw fedoras (the latter with deep raw silk bands), wafer-thin dress watches and monogrammed pinky rings. Suits were usually single-breasted, cut with a slim silhouette from lustrous mohair, duopionni silk, and nailhead worsted of rich solid hues. Tuxedos were black mohair or silk, sports jackets were discreetly patterned cashmere paired with gabardine slacks. Casual wear followed the golf-style wardrobe of alpaca cardigans with an easy drape and wide sleeves, and pique polo shirts.
While Sinatra had a brief flirtation with American Ivy-styled clothing in the mid-1960s – bought from the prestigious J. Press in New York – the late ‘50s and early ‘60s look of international urbane elegance is what he’ll be remembered for.