Sinatra’s Pink Shirt and Puppytooth Check in High Society

Frank Sinatra as Mike Connor in High Society (1956)

Frank Sinatra as Mike Connor in High Society (1956)


Frank Sinatra as Macauley “Mike” Connor, swaggering tabloid reporter

Newport, Rhode Island, Summer 1956

Film: High Society
Release Date: July 17, 1956
Director: Charles Walters
Costume Designer: Helen Rose


BAMF Style is fulfilling a timely request from Ryan to explore the puppytooth jacket, pink shirt, and tie worn by Frank Sinatra for his early scenes in High Society, the 1956 remake of The Philadelphia Story that found Sinatra acting with his idol, Bing Crosby. The film lives up to its title with an abundance of luxury cars, opulent homes, and plenty of champagne.

Though set in summer, Sinatra’s ensemble is a nice bold springtime look as the April showers turn to May flowers.

What’d He Wear?

In 1964’s ABC of Men’s Fashion, Hardy Amies describes dogtooth check as “a small zig-zaggy broken check, most effective in plain, contrasting colors such as black and white.” Also known as houndstooth or “pied-de-poule,” this duotone tessellated textile pattern traces its origins in the Scottish highlands.

In High Society, Frank Sinatra wears a jacket in a smaller-scaled houndstooth check often referred to as “puppytooth.” The subtlety of puppytooth check can make it a less flashy alternative to traditional houndstooth and can even appear solid gray from a distance, the perfect choice for Mike’s summer weekend at Newport where he has to look casual yet luxurious while making a good enough impression on the Lord clan to get his story.

Mike shares a moment with Tracy.

Mike shares a moment with Tracy.

The full cut of the 1950s could threaten to overwhelm a skinny man like Sinatra, but the jacket is well-tailored – likely by Sy Devore, his preferred tailor at the time – to flatter his physique rather than swamp him like the overly baggy jackets of the late 1980s. The darted jacket has wide, padded shoulders, high armholes, and a single back vent.

The single-breasted jacket has widely-notched lapels that roll to two gray plastic front buttons. The jacket’s closed quarters were characteristic of the ’50s, thought they’re more flattering for a slim man like Sinatra as he doesn’t look as bottom-heavy as a more corpulent gent would. The straight hip pockets are positioned below his waist, lined up with the lower of the two buttons, and closed with wide flaps. He wears a white linen kerchief in his welted breast pocket.

Liz Imbrie (Celeste Holm) leads Mike in song.

Liz Imbrie (Celeste Holm) leads Mike in song.

Sinatra’s light pink oxford cloth shirt injects a nice touch of bold yet subtle color to break up the monotony of his grayscale outfit. Like Cary Grant’s distinctive shirts in Notorious, this shirt has the seemingly incongruous combination of a button-down collar and double (French) cuffs.

The large button-down collar, very American with its Brooks Brothers origins, signals informality while the double cuffs – albeit soft ones – indicate a more formal approach to dressing. The incongruity fits with the setting: casual yet classy and definitively American.

Sinatra fastens his double cuffs with a set of dark onyx square links with rounded corners.

Spy Magazine's finest.

Spy Magazine‘s finest.

The thick black knit tie fills the collar space with a large Windsor knot.

Always a prankster...

Always a prankster…

The wider blade of the tie perfectly meets the fastening button of his jacket and the trouser waistband at Sinatra’s natural waist. He wears the menswear staple of dark gray flannel trousers, here with belt loops, side pockets, and the contemporary fashion details of reverse pleats and wide cuffs.

Mike experiences differing levels and types of discomfort at the Lord estate.

Mike experiences differing levels and types of discomfort at the Lord estate.

Mike coordinates his black leather belt to his shoes, a pair of black leather tassel loafers, a relatively new entry to the menswear arena after actor Paul Lukas commissioned his first pair from Alden in 1948. Sinatra’s loafers are likely also from Alden as no other manufacturers made the shoe until Brooks Brothers introduced its own tasseled slip-on in 1957. He wears his with black dress socks.

Mike makes the rounds.

Mike makes the rounds.

This being Sinatra, the outfit isn’t complete without a hat for the outdoor scenes. He wears a black pork pie made from Milan straw with a wide white pleated puggaree ribbon. A few years later, Frank would be illustrated wearing a very similar hat for the cover of his masterful 1958 concept album Come Fly with Me.

In a 2001 forum, Nancy Sinatra herself weighed in to confirm that this is almost definitely from Cavanagh, the hatmaker mentioned to be Frank’s favorite in Bill Zehme’s seminal The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Living.

One of Sinatra's iconic straw porkpie hats, seen on-screen and fooling around for Grace Kelly's camera behind the scenes.

One of Sinatra’s iconic straw porkpie hats, seen on-screen and fooling around for Grace Kelly’s camera behind the scenes.

Mike’s gold tank watch can be spied under his left shirt cuff, strapped to his wrist on a black leather bracelet.

Go Big or Go Home

Sinatra may be the first name that pops into your head when you think of iconic drinkers, but I wouldn’t recommend his tactic of singing to bartenders. In addition to the decreased chance of better service, there’s also a far increased chance of being removed from whatever drinking establishment you’re patronizing at the time.

I always liked that Scotch decanter behind the bar…

How to Get the Look

Mike Connor attempts to make up for his boorish attitude with a colorful and classy outfit, perfect for a spring or summer weekend spent hobnobbing among the rich and famous.

  • Black-and-white puppytooth check single-breasted 2-button jacket with notch lapels, welted breast pocket, straight flapped hip pockets, 3-button cuffs, and single back vent
  • Light pink oxford shirt with large button-down collar, front placket, and double/French cuffs
    • Dark onyx rounded-corner square cuff links
  • Black knit tie
  • Dark gray flannel reverse-pleated trousers with belt loops, side pockets, and turn-ups/cuffs
  • Slim black leather belt with silver-toned single-prong buckle
  • Black leather tassel loafers
  • Black dress socks
  • Gold tank-style dress watch on black leather strap
  • Black Milan straw porkpie hat with wide white pleated puggaree band

For a stylish finishing touch, Mike wears a classic white linen pocket square.

Do Yourself a Favor and…

Check out the movie.

The Quote

Inbreeding always produces idiots.


  1. Mark Gibson

    A great outfit, but Macauley Connor is quite a decent chap – a long way from a BAMF. Can I suggest Sinatra’s John Baron from Suddenly? A very sick puppy. However, Baron is only seen in one suit and it’s nothing that special. Or Joey Evans from Pal Joey. A singing BAMF, no less. Several sharp suits, black tie, white tie. And a band uniform which is very close to a cream linen tuxedo. Joey is essentially a con man so the film is something of a companion piece to Ocean’s Eleven. Or The Joker Is Wild, as another Joe – Joe E Lewis. Sinatra, BTW, gives a career-best performance in this role and it is astonishing that he was not even nominated for an Oscar. The material was just too dark, I guess.

    • luckystrike721

      Thanks for the great ideas, Mark! All terrific suggestions. I’ve been meaning to see Pal Joey for quite some time (Rita Hayworth and Kim Novak!) as well as The Joker is Wild. I have an old copy of Suddenly, but I understand there’s a much better formatted DVD out in the last few years, so I’ll need to pick it up.

      Much appreciated!

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