Cocktail: Tom Cruise’s Violet Four-Petaled Tropical Shirt

Tom Cruise and Elisabeth Shue in Cocktail (1988)


Tom Cruise as Brian Flanagan, ambitious tropical bartender

Ocho Rios, Jamaica, Spring 1988

Film: Cocktail
Release Date: July 29, 1988
Director: Roger Donaldson
Costume Designer: Ellen Mirojnick


As I’ve already stated in a few recent posts, I’m spending this week enjoying my honeymoon in Jamaica, the setting for a handful of James Bond movies as well as the critical flop but mega box-office hit Cocktail, released 35 years ago this summer.

Adapted from Heywood Gould’s semi-autobiographical novel of the same name, Cocktail stars Tom Cruise as Brian Flanagan, an ambitious and arrogant Army veteran with Wall Street dreams… and a TGI Fridays reality, as he begins working as a bartender to make money while attending business school.

Brian finds he has a knack for bartendering, specifically the flashy brand of flairtending taught to him by more experienced barman Doug Coughlin (Bryan Brown), with whom he partners at a trendy club and leaves his business ambitions behind. As with all friendships where both parties end up sleeping with Gina Gershon, the tension between Brian and Doug culminates in a very public blowout that results in Brian’s self-imposed exile to a beachside tourist bar in Jamaica.

Two years after their barroom brawl, the now-married but still-mischievous Doug arrives on the island and quickly makes amends with Brian… in fact, it’s almost jarring how quick Brian is to not only forgive but eagerly greet his manipulative old pal. And it’s almost jarring how quick Doug is to sabotage yet another of Brian’s romantic entanglements, knowing that the insecure Brian will take the bait when Doug challenges that he can’t take home any of the “moneyed females” in the bar, inadvertently causing Brian to ruin his budding relationship with the charming Jordan Mooney (Elisabeth Shue) when he sleeps with the cougar Bonnie (Lisa Banes). Was it worth it to win a $50 bet?

What’d He Wear?

Wall Street was Ellen Mirojnick’s previous costume design credit before Cocktail, which illustrated how effectively she could design for the beach as well as the boardroom. While Brian Flanagan may have once aspired to Gordon Gekko’s level of bespoke tailored suits, he seems happily at ease in his Jamaican wardrobe of oversized and brightly printed tropical shirts that contribute to the convivial atmosphere at the beachside bar he maintains.

For the pivotal sequence where Brian takes Doug’s bet to seduce Bonnie and ends up betraying Jordan, he wears an oversized long-sleeved silky shirt with a floral all-over print against a dark violet ground. The shirt has a point collar, non-matching breast pocket, and a plain front (no placket) that Brian wears with the top few white pearl-esque plastic buttons undone.

I don’t have the botanical expertise to determine if the print is meant to represent a specific flower or leaf, but I can tell you the overall shape reminds me of a windmill. Each four-petaled shape has a violet squiggle separating the pale pink blade from the white mid-section, with a pale-pink stigma in the center that is semi-bordered by a violet arc.

Tom Cruise in Cocktail (1988)

Brian’s favorite trousers in Jamaica are his white cotton medium-rise slacks, designed with short single pleats that contribute to their comfortably full fit. The wide belt loops go unused, and the trousers clearly fit Tom Cruise well enough that they’re able to remain in their intended position just below his natural waist without needing a belt. The trousers have slanted side pockets, button-through back pockets, and plain-hemmed bottoms with a tendency to bunch over the tops of his shoes when he doesn’t self-cuff them.

Brian wears the same white canvas deck sneakers that had him and Jordan pondering who invented the plastic “flugelbinders” at the ends of his white laces. An evolution of the Sperry CVO that was the world’s first non-slip deck shoe upon its invention in 1935, these follow the general “circular vamp oxford” closed-lace design that resulted in the CVO name, albeit with the unorthodox addition of an apron-toe seam.

Tom Cruise in Cocktail (1988)

In the nearly two years since he left New York, Brian must be doing well enough for himself tending bar at this tropical paradise that he was able to update his watch to a Rolex Air-King. Introduced in 1958 to honor the RAF pilots who flew during the Battle of Britain, the Air-King was Rolex’s entry Oyster Perpetual for decades, a downsized alternative to the Explorer model that had been introduced five years earlier. Brian’s stainless steel Air-King boasts a silver dial and is worn on a steel “Oyster”-style three-piece link bracelet.

Tom Cruise and Elisabeth Shue in Cocktail (1988)

Tom Cruise models Brian’s stylish Persol sunglasses and Rolex watch in a promotional photo with Elisabeth Shue.

As most of these scenes are set during the evening hours, even a cocky yuppie like Brian isn’t louche enough to wear his sunglasses at night—thankfully resisting Corey Hart’s synth-pop call to arms released four years earlier. That said, Brian’s tortoise square-framed Persol sunglasses are so stylish that he would almost be excused for doing so. Almost.

What to Imbibe

Bartender, serve thyself. Though they’re never mentioned by name, the cream-colored tropical long drinks that Brian mixes for himself and Doug are almost certainly the famous Piña Colada—the venerated rum, coconut, and pineapple concoction that was having something of a moment through the decade following the 1979 release of Rupert Holmes’ single “Escape (The Piña Colada Song)”.

Legend has it that the piña colada can trace its origins to the early 19th century Puerto Rican pirate Roberto Cofresí, who mixed cocktails of rum, coconut, and pineapple to boost his crew’s morale. Whether the account is true or not, it would be nearly a century after Cofresí’s death until the piña colada first appeared in print when Harry Craddock published a similar mix of ingredients in his 1930 publication of the Savoy Cocktail Book, stipulating white rum, coconut milk, and crushed pineapple, blended with ice. More claims to its invention—or at least perfection—were made as the decades passed, with Puerto Rican bartender Ramón “Monchito” Marrero credited with perfecting it with his 1954 recipe while working at the Caribe Hilton Hotel. The piña colada was named the official drink of Puerto Rico in 1978, just a year before Mr. Holmes appropriated it for his soft-rock ear-worm.

There are many different ways to make a piña colada, with the IBA stipulating five parts white rum, three parts coconut cream, and five parts pineapple juice, the latter essential as “piña colada” is literally Spanish for “strained pineapple”. According to the IBA, the three ingredients can either be blended or mixed together on the rocks, as long as they’re poured into the distinctively shaped poco grande glass.

Tom Cruise in Cocktail (1988)

Yes, Brian likes piña coladas, but the jury’s still out on his thoughts about dancing in the rain.

After accepting Doug’s bet, Brian moves across the bar to take Bonnie’s order. “A vodka on the rocks with a squeeze of lime” is hardly tropical enough for the environment, so he insists on instead making her a Jus D’Amour… which he helpfully translates as “juice of love,” in case his overall demeanor didn’t already telegraph his bedroom intentions with her.

In addition to white rum, sweet red vermouth, and a dark rum floater, Brian explains that his love juice is “made with fresh fruit, right off the vine… trust me when I tell you that it is nothing short of spectacular.”

Tom Cruise in Cocktail (1988)

You’d think Brian would know that the kind of person ordering a vodka on the rocks probably doesn’t want your blend of rums and fruit… even if she is interested in your juice of love.

I’m inclined to believe that Brian’s “spectacular” cocktail is a creation of his own, as contemporary searches for Jus D’Amour primarily yield a perfume marketed as “a love song in a bottle.”

How to Get the Look

Tom Cruise in Cocktail (1988)

Tropical bartender Brian Flanagan maintains his own uniform of loose and flowy printed shirts with white trousers and deck sneakers while mixing up rum-soaked cocktails for privileged vacationers, flashing the fruits of their tips via a Rolex strapped to his wrist.

  • Violet four-petaled floral print silky long-sleeved shirt with point collar, plain front, button cuffs, and breast pocket
  • White cotton flat front trousers with self-suspended waistband, slanted side pockets, button-through back pockets, and self-cuffed plain-hem bottoms
  • White canvas four-eyelet deck sneakers with white outsoles
  • Rolex Air-King stainless steel watch with silver dial and steel Oyster-style link bracelet

Do Yourself a Favor and…

Check out the movie.

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