Cocktail: Tom Cruise’s Spattered Pink Tropical Shirt

Tom Cruise as Brian Flanagan in Cocktail (1988)

Tom Cruise as Brian Flanagan 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


I will admit that I’m not the biggest fan of Cocktail, but I’ve been in a tropical mood lately so this colorful, super-’80s yarn of bartending and bonking felt like a perfect summertime post in advance of Tom Cruise’s birthday tomorrow.

By all accounts, this winner of two Razzies should have been better, and author Heywood Gould has voiced considerable disappointment that his more serious source novel underwent such commercialization that the end product was primarily a vapid celebration of Tom Cruise using the daiquiri recipe he learned at TGI Friday’s to try to get laid as much as he could.

And yet, Cocktail has remained a part of pop culture more than 30 years after its ignominious release, whether you consider all the times you’ve heard the Beach Boys’ “Kokomo” or if you’ve patronized bars like Coughlin’s Law, a local Pittsburgh tavern that clearly took inspiration from the philosophy espoused by Bryan Brown’s character.

Cruise stars as Brian Flanagan, a swaggering Army veteran with dreams of becoming a millionaire despite little to get him there aside from some business classes and an overwhelmingly toothy grin. He supports himself by slinging cocktails a TGI Friday’s under the tutelage of Doug Coughlin (Brown), a hubristic cocksman from Down Under. After the incorrigible Coughlin proves a little too reckless with his swizzle stick, Brian abandons his mentor and flees to the warm comfort behind a beachside bar in Jamaica.

More than a year later, Coughlin stumbles into Dragon Beach with his new beautiful bride in tow, convincing Brian that any future girlfriends of his would be safe from his former mentor’s muddler… just in time for him to meet Jordan Mooney (Elisabeth Shue), a charming tourist who doesn’t rely on her family’s money to fuel her own artistic ambitions. After she writes off their first encounter as a one night stand, he continues the relationship over a series of dates that range from sketching each other in the sand to pondering the genius who cornered “the flugelbinder market.”

What’d He Wear?

Cocktail features the costume design of Ellen Mirojnick, a prolific designer who dressed some of the most iconic characters of the ’80s—e.g. Michael Douglas as the slick-haired and slick-suited Gordon Gekko in Wall Street—and Cocktail proved that Mirjonick could design just as effectively for the beach as for the board room.

Brian’s Jamaican wardrobe consists almost exclusively of bright, colorful printed shirts that undoubtedly contributed to the atmosphere of levity that his beachside patrons are looking for behind their parade of piña coladas. When Brian steps out from behind the bar for fun in the sun with Jordan, he wears a chaotically patterned camp shirt, designed in an abstract all-over print of pink, yellow, and lilac streaks, all overlaid by the occasional black spatter. Brian buttons most of the mother-of-pearl buttons up the plain “French placket” front, leaving a few open at the top that work with the fashionably oversized fit to create a roomy appearance as illustrated by the elbow-length sleeves enveloping his arms.

Tom Cruise as Brian Flanagan in Cocktail (1988)

The shirt’s long, untucked hem and the fact that Brian remains seated covers the top of his white cotton trousers, but we can assume they’re identical to the white flat front pants we see elsewhere, which have a self-suspended waistband with wide belt loops that go unused, slanted side pockets, and button-through back pockets. Brian rolls up the plain-hemmed bottoms to create a louche self-cuffed effect.

Tom Cruise as Brian Flanagan in Cocktail (1988)

Talking about the makers of ashtrays and cocktail umbrellas prompts Brian to wonder who makes the plastic ends of his shoelaces, which Jordan offers may be called “flugelbinders”. He kicks up his left foot to allow himself a visual aid, examining his deck sneaker with its white canvas uppers and the white laces fed through four oxford-style lace eyelets. Apropos the tropical climate and casual context, Brian foregoes socks (or wears very low “no-show” hosiery.)

At first, I had thought Cruise was wearing the famous Sperry CVO model that had included wearers ranging from Paul Newman to Mr. Rogers since its development as the first nonslip deck shoe in 1935, but the addition of an apron-toe seam and the flat, non-siped sole suggests that even an ’80s materialist like Brian isn’t sporting the wares of a brand that had been so prominently touted in Lisa Birnbach’s The Official Preppy Handbook published at the start of the decade.

Tom Cruise as Brian Flanagan in Cocktail (1988)

Jordan hides her disappointment that Brian’s deck sneakers don’t have Sperry’s signature siped soles.

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.

Cruise may have flown to fame peering through Ray-Bans in Risky Business and Top Gun, but he switches eyewear loyalties in Cocktail as he takes in the sights of Jamaica through a pair of tortoise Persol  PO3225S sunglasses. With a straight top bar, these Persols echo the Ray-Ban Wayfarers from Top Gun but with the addition of Persol’s brand signatures from the silver sword-shaped arrows over the temples to the keyhole-cut bridge. As of June 2021, Persol has rereleased the PO3225SS model, available via Amazon and

Tom Cruise as Brian Flanagan in Cocktail (1988)

A brief vignette of Brian and Jordan walking through Ocho Rios indicates that the duo have swimming on the agenda, as Brian has swapped out his trousers for a pair of black polyester Speedo swimming trunks… though neither of their swimwear lasts long during the pair’s famous romp in Dunn’s River Falls.

Tom Cruise as Brian Flanagan in Cocktail (1988)

While the Speedo name may bring to mind briefs with inseams shorter than some men may be comfortable with, the English brand continues offering swim trunks of a more conventional length as worn by Cruise in Cocktail, such as the black polyester Speedo Redondo still available from Amazon as of June 2021.

How to Get the Look

Elisabeth Shue and Tom Cruise in Cocktail (1988)

Elisabeth Shue and Tom Cruise in Cocktail (1988)

As tropical-printed camp shirts continue their revival this summer, Tom Cruise’s swaggering bartender in Cocktail provides a straightforward template for how to dress (but not how to behave!) for a summer fling in the sun, accessorizing his spattered shirt, white trousers, and deck shoes with Persol shades and a Rolex.

  • Pink, yellow, and lilac-streak (and black-spatter) printed short-sleeve camp shirt
  • 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
  • Persol PO3225S “Havana” tortoise rectangular-framed sunglasses with green lenses
  • Rolex Air-King stainless steel watch with silver dial and steel Oyster-style link bracelet

Do Yourself a Favor and…

Check out the movie and try to track down Heywood Gould’s source novel.

The Quote

Before you know it, your life is just one long night with a few comatose daylight hours.


  1. Cecil Selkirk

    Love this movie. I remember reading a review of it at the time that said “the worst movie of the year (Cocktail) had produced the best song of the year (Don’t Worry, Be Happy).” Great review, thank you.

  2. Pingback: Risky Business: Tom Cruise in Donegal Tweed » BAMF Style

Leave a Reply