Vitals

Bing Crosby as C.K. Dexter Haven, jazz musician

Newport, Rhode Island, Summer 1956

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

Background

Happy St. Valentine’s Day! This year’s theme for the #WeekOfWeddings seems to be impromptu nuptials that find our cheeky protagonists thrust into taking the vows without a chance to don traditional wedding attire. Today, we’re following a mischievous summer weekend among the socialites of Newport, Rhode Island, in High Society, the musical remake of The Philadelphia Story.

High Society recasts The Philadelphia Story‘s leading gents Cary Grant and Jimmy Stewart with the more musically inclined Bing Crosby and Frank Sinatra, respectively, though it’s interesting to note that Crosby is actually a few months older than Grant, making this surely one of the few times in movie history that a remake actually featured a performer older than his or her predecessor!

Katharine Hepburn’s role was recast with Grace Kelly, establishing High Society as the actress’ final film role before her retirement at the age of 26 upon marriage to Prince Rainier III of Monaco. In the spirit of marriage, Kelly wore her actual Cartier engagement ring from Rainier on screen.

What’d He Wear?

Other than his tuxedo, Bing Crosby’s primary wardrobe as C.K. Dexter Haven in High Society consists solely of blazers and spectator shoes, a signature look for the moneyed man of leisure in the 1950s.

Dexter’s first blazer is a navy hopsack wool (or wool-and-mohair blend) single-breasted jacket with notch lapels that roll to a two-button stance, with the buttoning point placed perfectly at the natural waist to meet the top of the trousers. Both the front buttons and the three smaller buttons on the cuffs of each sleeve are smooth gold-toned shank buttons.

The blazer has a single back vent, jetted hip pockets, and a squared patch breast pocket adorned with a shield-shaped stitched crest. The crest appears to be illustrated with a black-and-white horse on a light blue ground with a blue trim that just slightly contrasts against the darker navy of the blazer’s wool jacketing.

Like many other actors of the era, Bing Crosby was known to have worn his own clothing in his films, so it’s possible that this blazer carries the crest of one of the at least 75 golf clubs to which he was a member, although the appearance of a horse (or a horse-like shape) may signify the possibility of a riding club.

Dexter’s first appearance finds him totally in leisure, smoking his pipe while enjoying the sounds of Louis Armstrong’s band. He wears a cotton open-neck shirt in a light blue and white mini-gingham check with a long point collar and button cuffs.

The next time we see Bing in this blazer, he’s wearing it with a plain white shirt, similarly styled with a long-pointed semi-spread collar, single-button rounded cuffs, and a plain front. He has also added a white pocket square, neatly folded into the breast pocket of his blazer for an added touch of formality that will come in handy for his impromptu wedding.

Luckily for Dexter, this white shirt and pocket square adds a higher touch of formality to the outfit than his gingham shirt the previous day, making it far more easy for him to don Mike Connor’s repp tie and look decent enough to impulsively marry his ex-wife Tracy (Grace Kelly).

As the exuberant Spy Magazine reporter Mike Connor, Frank Sinatra wore a sharp dark navy suit with a blue-on-navy striped tie that he was all too happy to lend to Dexter. The tie’s blue “downhill” diagonal stripes are spaced about an inch apart, alternating in width over the navy ground.

Perhaps I’m partial to this outfit because Bing pairs his blazer with gray trousers, my personal preference, rather than khakis. The blazer’s first appearance, with the open-neck gingham shirt, finds it paired with light blue-gray pleated trousers. Later, when wearing a white shirt and striped tie for his re-marriage to Tracy, he sports a pair of darker gray flannel trousers.

Both pairs of gray trousers are pleated with turn-ups (cuffs). He always wears his blazer buttoned, concealing the trouser waistband.

Dexter wears brown-and-white spectator oxfords, and his caddish personality corresponds to this footwear’s original “correspondent shoe” connotations as they were evidently favored by men described as “correspondents” in British divorce cases.

These particular shoes have dark chestnut brown leather medallion toe cap, heel cap, and lace panels with a white leather vamp. They appear to be full brogues but with straight toe caps rather than the wingtips commonly associated with full brouging. He wears them with charcoal gray cotton lisle socks.

To see how Cary Grant’s C.K. Dexter Haven dressed for a day of leisure that turned into his wedding day, check out his collarless jacket in The Philadelphia Story.

What to Imbibe

After a particularly rough pre-wedding night, Tracy Samantha Lord (Grace Kelly) is prescribed a hair of the dog recovery by her ex, C.K. Dexter Haven (Bing Crosby):

…the juice of a few fresh flowers called a Stinger. Removes the sting.

The Stinger is one of many classic cocktails that all but disappeared from the American mixology scene around the 1970s. It traces its origins to, appropriately enough, the “high society” elite of Edwardian era New York City when it was considered a post-prandial digestif rather than a cocktail.

A century later, the Stinger seems to have eluded the renewed interest in classic cocktails that revived the Manhattan and Old Fashioned on the menus of hip watering holes, though it was a staple of mid-century pop culture with references to the drink appearing in novels like Diamonds are Forever, The Price of Salt, and The Spy Who Came in From the Cold as well as films including The Bishop’s Wife, In a Lonely Place, The Apartment, and the original cinematic version of this tale, The Philadelphia Story. A mention in Mad Men‘s first season failed to revive the drink to the same extent as Don Draper’s preferred Old Fashioned, and your best bet for a Stinger these days would be to make your own… so let’s explore that!

All you need for a Stinger is two central ingredients: brandy and white crème de menthe. (Green crème de menthe works in a pinch for the same taste, but it will look rather muddy… and you don’t want to be the sort of person who would offer a glass of mud to Grace Kelly, do you? Ray Milland, on the other hand…)

Ratios differ by taste palettes, of course, but common practice is a 3-to-1 ratio of cognac to crème de menthe, poured together in a mixing glass filled with ice, stirred, and strained into a chilled cocktail glass or a rocks glass over ice; the latter became a more popular practice following Prohibition when drinkers were approaching the Stinger as a traditional cocktail rather than a strictly after-dinner drink.

How to Get the Look

Bing follows a traditional template for classy yet dressed-down leisure attire… as well as proving the outfit’s versatility when he is pulled into a more formal situation with no time or opportunity to change.

• Navy blue hopsack wool/mohair single-breasted 2-button blazer with crest-embellished patch breast pocket, straight jetted hip pockets, 3-button cuffs, and single back vent
• White or light blue gingham cotton shirt with long-pointed collar, plain front, and 1-button rounded cuffs
• Gray flannel pleated trousers with side pockets and turn-ups/cuffs
• Dark brown-and-white leather spectator oxford brogues with medallion toe-cap
• Charcoal gray cotton lisle socks
• Gold round-cased wristwatch with white dial on curved brown tooled leather strap (with a gold single-prong buckle)

If there’s no charming Sinatra-type around to lend you his tie in a flash, you can check out the classic repp ties from Brooks Brothers… particularly this BB#3 Rep Slim Tie in navy and light blue. Look familiar?

Do Yourself a Favor and…

Check out the movie.