Come Fly With Me: Sinatra’s Jet-Setting Style

Frank Sinatra, flanked by the stewardesses of his Trans-Canada Air Lines flight, circa 1950. The dawn of the "jet age"—and the best years of Frank's career—were yet to come.

Frank Sinatra, flanked by the stewardesses of his Trans-Canada Air Lines flight, circa 1950. The dawn of the “jet age”—and the best years of Frank’s career—were yet to come.


Frank Sinatra, multi-talented entertainer and Rat Pack crooner

Part of BAMF Style’s Iconic Photo Series, focusing on style featured in famous photography of classic stars rather than from specific productions.


Sixty two years ago this week, on January 6, 1958, Frank Sinatra released his ninth concept album for Capitol Records, Come Fly With Me. Anchored by the title track specifically penned for Frank by Sammy Cahn and Jimmy Van Heusen, the album celebrated the contemporary Jet Age, specifically the chic “jet setters” who were able to afford the luxurious amenities offered by BOAC and Pan Am flights that would spirit them between London and New York, Paris and Rome, and Hong Kong and Tokyo.

The album, which was Sinatra’s first collaboration with arranger and conductor Billy May, ascended like a state-of-the-art Boeing to #1 on the Billboard album charts in only its second week and would be nominated for Album of the Year at the first annual Grammy Awards, held May 4, 1959, at the Beverly Hilton Hotel in Los Angeles.

In the spirit of Frank’s musical trip around the world on this #SinatraSaturday, let’s take a look at how the Rat Pack leader himself dressed “where the air is rarified…”

In these studies of Sinatra’s style explored below, you’ll notice some overlapping themes: sharp suits with unique lining, light shirts and slim ties, printed silk pocket squares, and a travel-friendly trilby.

1961: London

Frank Sinatra leads fellow Rat Packer Dean Martin across the tarmac as they greet fans at Heathrow Airport, August 1961.

Frank Sinatra leads fellow Rat Packer Dean Martin across the tarmac as they greet fans at Heathrow Airport, August 1961.

Frank Sinatra and Dean Martin were extensively photographed when they arrived at London’s Heathrow Airport on August 4, 1961. Although it was the middle of summer, Frank was dressed for the mild English summer climate in a dark flannel three-piece suit though he topped his look with a seasonal dark straw short-brimmed trilby with a wide white puggaree ribbon.

The much-photographed arrival left no detail of Frank’s suit unseen. The single-breasted jacket has notch lapels that roll to a two-button front, three-button cuffs, the usual straight flapped hip pockets, and a welted breast pocket where Frank wears a dark patterned silk pocket square. His five-button waistcoat has a considerably low fastening point and a notched bottom, and it appears to have been designed to be worn with all five buttons fastened.

Frank’s double reverse-pleated trousers are worn sans belt as most sartorialists would advise with a three-piece suit, though the rigors of travel and no doubt a few drinks to steady the singer’s nerves during the international flight took their toll on Frank’s waistline and the trousers are sagging a bit by the time he hits the tarmac, revealing a little more of the trouser waistband—as well as the bottom of his white shirt—than should usually be seen with a waistcoat. The double-cuffed shirt has a pinned collar with plenty of tie space to accommodate a neatly patterned tie with a repeating series of light circles against a dark ground, knotted in a Windsor or half-Windsor knot.

The trousers are finished with turn-ups (cuffs) on the bottoms, breaking high over his low-contrast socks and a surprising pair of patent leather opera pumps. “Shine your mary janes on the underside of a couch cushion,” Frank advised via Bill Zehme’s seminal tome The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’. Also known as court shoes in the UK, these are almost always constructed with black patent leather uppers with a ribbed grosgrain silk bow on the vamp. These classic men’s evening shoes are most associated with white tie or more formal black tie dress codes (and are increasingly rarely seen with those), and it’s a surprise to see Sinatra wearing them in this less-than-formal daytime context.

“The gleam of his patent leather mary janes, with grosgrain bows—his ‘party heels’—was essential to his well-being,” wrote Zehme. “‘You like my mary janes?’ he asked a Paris audience in 1962. ‘You like the little black bows on ’em, nice and shiny?'”

While security measures have changed drastically in the nearly 60 years since Ol’ Blue Eyes alighted at Heathrow, the ease with which Frank’s opera pumps would slip off and on at a TSA checkpoint would indeed make them a more convenient—if excessively stately—footwear option for the modern traveler.

As usual, Dean Martin is looking rather stylish with a dash of his typical insouciance. Dino may be dressed in the same gray wool suit he wore the previous year opposite Frank in Ocean’s Eleven (1960).

1962: Cal-Neva

An introspective-looking Sinatra thumbs open a deck of Camels while flying to the Cal-Neva Lodge, 1962. Photo by Ted Allan.

An introspective-looking Sinatra thumbs open a deck of Camels while flying to the Cal-Neva Lodge, 1962. Photo by Ted Allan.

In 1960, nine years after Frank Sinatra’s first near-fatal visit to Cal Neva Lodge & Casino, the singer bought the Lake Tahoe resort with partners that included Dean Martin, Frank’s manager Hank Sanicola, “Mr. Atlantic City” Paul “Skinny” D’Amato, and—allegedly—Chicago Outfit boss Sam Giancana. Within two years, Frank had expanded his ownership from 25 to 50%, splitting the remaining half between Sanicola and pugnacious casino executive Sanford Waterman.

Under Frank’s leadership, Cal-Neva hosted lavish parties where Hollywood celebrities including his Rat Pack pals, Lucy and Desi, Judy Garland, Kim Novak, Tony Curtis, and—of course—Marilyn Monroe reportedly rubbed elbows with mobsters like Giancana who took advantage of the privacy of the Prohibition-era tunnels installed on the property. Sinatra welcoming Giancana to the Cal-Neva led to the dissolution of his business relationship with Sanicola, who was reasonably concerned with hosting a gangster who was otherwise banned from entering any casino in the state of Nevada. But I digress.

In the spring of 1962, Frank Sinatra embarked on an ambitious world tour to benefit children’s charities around the globe. That April, Sinatra started in Mexico City before his chartered Boeing 707 whisked him around the globe to perform in prime “jet set” destinations such as Tokyo, Hong Kong, Israel, Greece, Italy, France, and London, before he was back in the U.S. for a few summer gigs at the Cal-Neva, the Sands, and D’Amato’s 500 Club in Atlantic City. Along for the tour was photographer Ted Allan, who captured every moment of the entertainer whether he was live on stage or at leisure.

Aboard Sinatra’s personal Martin 404 plane en route the Cal-Neva Lodge, Allan took several shots of a stylish and serious-looking Sinatra, dressed in one of a gray sharkskin wool suit with a blue duo-tone block-striped tie, red-and-blue-on-beige paisley silk pocket square, and a light blue Oxford cloth cotton shirt with button-down collar and button cuffs, far less fussy than the pinned collars and French cuffs of his usual shirts.

1964: One for the Road

Frank Sinatra, photographed by Yul Brynner, 1964.

Frank Sinatra, photographed by Yul Brynner, 1964.

One of the most enduring images in Ol’ Blue Eyes lore has been the famous photograph snapped by his pal Yul Brynner in 1964 as Sinatra was descending from a helicopter in his standard attire of a dark suit—undoubtedly tailored by the venerable Sy Devore—with a colorful silk pocket square and one of the many Cavanagh hats he never left home without.

In his hand, the item that makes the photo complete: a rocks glass likely full of Frank’s preferred elixir, Jack Daniel’s Tennessee Whiskey.

“Together they traveled the world, a man and his sour mash whiskey, ten cases in every cargo hold beneath him, lest any foreign destination be without supply,” wrote Zehme. “How he liked it: Always three or four ice cubes, two fingers of Jack Daniel’s, the rest water, in a traditional rocks glass.”

Do Yourself a Favor and…

Check out Frank Sinatra’s classic 1958 album Come Fly With Me (which sounds great on vinyl!)

I also highly recommend reading The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’ by Bill Zehme. My good friend Teeritz, the writer of a fantastic blog in its own right, sent me a copy several years ago that I find myself reading quite frequently.

The cover of Frank Sinatra's 1958 album Come Fly with Me.

The cover of Frank Sinatra’s 1958 album Come Fly with Me.

William Stadiem’s book Jet Set also shines an extensive look at this glamorous era, with a chapter dedicated to Sinatra excerpted at The Daily Beast that touches on the singer’s somewhat ironic fear of flying, his “altruistic” 1962 world tour, and the ultimate irony when his beloved mother Dolly died in a plane crash on January 6, 1977, 19 years to the day after her successful son had released the album Come Fly With Me.


  1. Corinth Arkadin

    As normal, Excellent write-up.

    This is getting to be a daily check for me, as much as reading a newspaper.

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  4. Gary Wells

    Excellent reporting here, sir. Did not know Brynner took that iconic picture. The Way You Wear Your Hat I bought and read at the outset of my fascination with FS and his peers. Required reading.

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