The Talented Mr. Ripley: Dickie’s Black and White at Sea

Jude Law as Dickie Greenleaf in The Talented Mr. Ripley

Jude Law as Dickie Greenleaf in The Talented Mr. Ripley (1999)


Jude Law as Dickie Greenleaf, narcissistic profligate playboy

Italy, Summer 1958

Film: The Talented Mr. Ripley
Release Date: December 25, 1999
Director: Anthony Minghella
Costume Design: Ann Roth & Gary Jones

WARNING! Spoilers ahead!


Last year around this time, I finally read Patricia Highsmith’s thriller novel The Talented Mr. Ripley that provided the source material for two stylish adaptations: the lush French production Purple Noon (Plein soleil) released in 1960 and Anthony Minghella’s more faithful The Talented Mr. Ripley released on Christmas 1999.

The central drama follows a trio of American jet-setters cavorting on Italy’s scenic Amalfi Coast: spendthrift playboy Dickie Greenleaf (Jude Law), his charming on-and-off girlfriend Marge Sherwood (Gwyneth Paltrow), and their mysterious companion Tom Ripley (Matt Damon), who seems to have taken an obsessive interest in Dickie.

At first, Dickie seems no more than mildly annoyed by the newcomer, loosened somewhat when he and Marge are entertained by Tom’s “uncanny” ability to impersonate and mimic his own father.

Marge: [Tom] made me laugh so hard I almost got a nose bleed!
Dickie: Is that good?
Marge: Shut up.

Weeks of constant companionship, homoerotic baths, and awkward fashion swaps deteriorate relations among the trio, which come to a head as Dickie rents a boat with Tom and sails it off the Sanremo coast, where he intends to move both to ditch Tom, whom Dickie declares can be “a leech” and—even worse—”quite boring.” As Dickie states:

I really, really do not want to be on this boat with you.

Fed up, Tom takes the opportunity to throw it all back in Dickie’s face… literally. With an oar.

What’d He Wear?

After their first official meeting on the beach (filmed at Bagno Antonio in Ischia), Dickie again encounters Tom lunching with Marge in his absence. Dickie wears a laidback but eye-catching wardrobe of black shirt and white trousers, communicating his simpler approach to life than the more complex Tom.

For this lunch as well as their last day together on that fateful boat trip, Dickie sports the same unique black short-sleeved shirt, worn only partially buttoned and untucked with a pair of off-white trousers on both occasions. This initial appearance clearly illustrates the contrast between the easygoing Dickie and the buttoned-up Tom in his Ivy garb, while comparing their outfits on the boat shows just how extensively Tom has been influenced by Dickie, right down to his new clothing.

Dickie’s black sport shirt is softly constructed from a narrowly ribbed cloth, so lightweight that it appears almost sheer under the Mediterranean sun. The shirt has at least six black sew-through buttons up the front, ostensibly to be fastened up to the neck, and a patch pocket over the left breast.

Jude Law in The Talented Mr. Ripley

Dickie Greenleaf eyes the newcomer with some suspicion.

Although costume designers Ann Roth and Gary Jones worked with John Tudor in New York to make Dickie’s clothing, shirts like this are unlike almost anything produced by American manufacturers of the era and accurately reflect what someone like Dickie would have worn to comfortably show off while living la dolce vita in the more fashion-forward Europe.

Dickie offsets the darkness of the shirt by rotating it against his favorite white trousers, held up by a black leather Gucci belt identified by its telltale silver “G”-logo buckle. These provide an appropriately maritime cast to his style at sea, as he kicks back in a pair of white cotton double reverse-pleated trousers with belt loops, side pockets, back pockets, and turn-ups that he insouciantly self-cuffs even higher on each leg.

Jude Law and Matt Damon in The Talented Mr. Ripley

Tom has clearly been influenced by Dickie’s sense of style, now wearing silky sport shirts rather than the Ivy-style OCBDs from his arrival.

Having worn white leather moc-toe loafers in the city, the seagoing Dickie pulls on his more casual sneakers with white canvas uppers, flat white woven laces, and wide white rubber soles. Right down to the navy foxing stripe banded around the top of each rubber outsole, these oxford-laced sneakers resemble the classic Sperry Cloud CVO Deck Sneakers.

When we pan over the blood-stained shoes that he kicked off during the murder, we can spy dark blue insoles with double sets of white stripes on each side flanking the letter “E”—presumably the last letter of the manufacturer’s name—as well as the flattened heels that allow Dickie to wear them like slip-on clogs.

Jude Law and Matt Damon in The Talented Mr. Ripley

I’ve seen Sperry line some of their sneakers with striped insoles, though I don’t recognize this particular stripe arrangement. (And it’s possible that the errant “E” follows an “SP” and preceded an “RRY” that was removed by the costume team.)

Dickie often takes to the water in a unique deck jacket made of white duck, with an irregular stepped closure consisting of a series of six oversized grommets and hooks. This closure system may have been inspired by the U.S. Navy implementing “hook” deck jackets in 1943 to replace the earlier models with zippers that were often rendered inoperable by freezing rain or corrosive salt water.

The front of Dickie’s hip-length jacket is split into a straight, funnel-like top portion that can fold down like a traditional collar and a more dramatic asymmetrical flap that tapers from a sharp corner on the right side of the chest down to the hem. Both these top and lower portions are each rigged with three nickel-finished grommets that coordinate to matching hooks on the right side of the jacket. The jacket also has a horizontal-zip set-in pocket over the left breast and set-in sleeves that are finished with short vents at each cuff.

Jude Law and Matt Damon in The Talented Mr. Ripley

Once the duo get acclimated in the boat, Dickie takes off his jacket, thus leaving it clean enough for Tom to pull on upon reaching dry land immediately after the murder… signaling that his programmatic takeover of Dickie’s identity has already begun.

Options are limited, but this jacket appears to mimic the spirit—and designer exclusivity—of something Dickie Greenleaf would have favored:
  • Ralph Lauren Purple Label Chester Canvas Deck Jacket in "classic cream" cotton (Ralph Lauren, $1,189)
Price and availability current as of July 2022.

Dickie sports a gold ring on each hand, with a double-ridged band on the middle finger of his right hand and a flashier ring with a green stone gleaming from his left pinky. Dickie describes the latter as a gift from Marge that he “had to promise—capital P—never to take it off.”

Dickie wears his stainless steel watch that follows a retro design suggesting Bulova, Hamilton, Longines, or Wittenauer, though BAMF Style reader Scott has shared a Spotern link concluding that Dickie likely wears an inexpensive Japanese-made Swanson wristwatch. The vintage-inspired timepiece has a round silver dial detailed with a diamond at the 12 o’clock position and Arabic numerals marking the 3, 6, and 9 o’clock hours. Dickie wears it on a mesh-like “Milanese” bracelet that closes with a single-prong buckle over his left wrist.

Jude Law in The Talented Mr. Ripley

“My job was to show this very well-off boy, Dickie, in Europe, on a very strict allowance, but with a sensational lifestyle,” costume designer Ann Roth explained to The Rake. “I had him in a jacket and some shorts, or a jacket and some linen trousers, and that jacket had to reflect a very rich background. And if he had one or two made in Rome, it had to look that way.”

When taking Tom into town after lunch, Dickie debuts the dark navy dupioni silk blazer that he would later wear with a pork-pie hat, two-toned shoes, and striped tie during their trip to Rome. The single-breasted jacket has straight peak lapels, three silver-finished shank buttons, a welted breast pocket, patch hip pockets, double vents, and three cuff buttons.

Jude Law and Matt Damon in The Talented Mr. Ripley

Dickie shows Tom around Mongibello.

What to Imbibe

When Tom meets the couple, he shares a concern that he’s intruding until Dickie abruptly asks: “Can you mix a martini?” “Sure,” Tom replies, but Marge breathes a sigh and states, “I mix a fabulous martini,” leaving the two “classmates” to catch up. “Everybody should have one talent,” Dickie jokes about Marge’s mixological abilities.

Weeks later, we finally see Dickie drinking one of Marge’s martinis, garnished with a single olive, as he and Freddie Miles (Philip Seymour Hoffman) otherwise ignore both Marge and an increasingly bitter Tom on a sailing trip off Mongibello.

Jude Law and Philip Seymour Hoffman in The Talented Mr. Ripley

In happier times—for Dickie, rather than Tom—Dickie enjoys a Marge-made martini with his fellow jazz hound Freddie Miles.

Patricia Highsmith, the author of The Talented Mr. Ripley, chronicled frequently enjoying martinis herself, with at least two mentions in her diaries of drinking seven martinis in one sitting. “I wonder if any moment surpasses that of the second martini at lunch, when the waiters are attentive, when all life, the future, the world seems good and gilded (it matters not at all whom one is with, male or female, yes or no),” she wrote.

How to Get the Look

Jude Law and Matt Damon in The Talented Mr. Ripley

Jude Law and Matt Damon in The Talented Mr. Ripley (1999)

Dickie Greenleaf’s wardrobe has come to exemplify resort fashion, blending the elegance of a bygone era with an insouciant nonchalance illustrated by the way he wears his clothing, only partially buttoning up his untucked black ribbed sport shirt, self-cuffing the bottoms of his already-cuffed white linen slacks, and stepping down the heels of his worn-in white sneakers to transform them into slip-ons.

  • Black narrowly ribbed short-sleeve button-up sport shirt with patch-style breast pocket
  • White linen double reverse-pleated trousers with belt loops, side pockets, button-through back pockets, and turn-ups/cuffs
  • Black leather Gucci belt with silver-toned “G”-logo buckle
  • White canvas oxford-laced CVO-style deck sneakers with navy foxing stripes and white rubber outsoles
  • Steel wristwatch with silver dial on silver Milanese mesh bracelet
  • Gold double-ridged ring
  • Gold signet pinky ring with green stone

Do Yourself a Favor and…

Check out the movie and read Patricia Highsmith’s novel.


I know, I’m late. I’m a swine.

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