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!
As this summer continues into August, so too did summer advance for the idiosyncratic trio of rich Amalfi Coast playboy Dickie Greenleaf (Jude Law), his girlfriend Marge Sherwood (Gwyneth Paltrow), and their pathological companion Tom Ripley (Matt Damon) in Anthony Minghella’s 1999 adaptation of Patricia Highsmith’s classic psychological thriller The Talented Mr. Ripley.
Spending time with Marge and Dickie allows Tom Ripley to grow increasingly enamored with the latter, and the young con artist manipulates an opportunity for the couple to insist that he remain with them at the picturesque seaside villa in Mongibello. After Tom literally drops his bait, a collection of American jazz records, all that the bebop-loving Dickie needs to hear is Tom’s declaration that Charlie “Bird” Parker is “a god” for Dickie to not only invite the strange young man to stick around but also to accompany him to a jazz club in Naples.
What began as a fun summer romp for the trio quickly grows tiresome for Dickie, who loses his pregnant mistress Silvana (Stefania Rocca) to suicide and finds the obsessive Tom Ripley to be increasingly tiresome himself, despite Tom offering to take the blame for the conditions that led to Silvana drowning herself after the father of her unborn child refused to help her. To the destructive Dickie, who deals with the tragedy by retreating to the familiar comforts of his saxophone, it may seem like merely a moment of misguided selflessness on Tom’s part, but it’s actually a long game in Tom’s long con to take over Dickie’s life.
What’d He Wear?
Ann Roth and Gary Jones, nominated for a well-deserved Academy Award for their costume design in The Talented Mr. Ripley, artfully juxtaposed the faux Ivy League grad Tom Ripley’s style with the laidback opulence of Dickie Greenleaf’s warm-weather wardrobe for days and nights on the Amalfi Coast.
One distinctive piece of Dickie’s wardrobe that appears during a few significant scenes in The Talented Mr. Ripley is this white knit resort shirt with its gray mesh-textured chest panels, each flanked on the outside by a slim black stripe. The material may be a softly knit cotton or a more luxurious fabric like cashmere.
The chest panels are bisected by a white-shadowed gray stripe down the center that. The stripes and chest panels end above the bottom, a white banded hem about two inches tall. The shirt has six flat white mother-of-pearl four-hole sew-through buttons up the plain front, including one on the bottom hem and one just below the sharp, wide revere collar.
Dickie wears the shirt with his favorite cream-colored lightweight trousers, hand-cuffed at the plain-hemmed bottoms. Their medium-high rise buries the waistband well under the shirt, but Dickie’s practice of wearing his lowest shirt buttons undone showcases the trousers’ long and luxurious double reverse pleats flanking the fly as well as the telltale “G”-shaped silver buckle of his black leather Gucci belt.
Dickie had first been seeing wearing this shirt with his own pale pink Bermuda shorts, another garment that makes a few appearances in the film though they don’t fare quite as well as his others in Bustle’s article ranking his shorts to commemorate the film’s 15th anniversary. The shorts close with an extended waistband tab, appear to have side adjusters in lieu of belt loops, and are once-cuffed at the wide-opening bottoms. Dickie would later wear them with his white diamond-textured short-sleeved polo shirt.
After a few years out of vogue in men’s fashion, colorful shorts have firmly regained a foothold—or leg-hold—in American menswear, and few can travel to popular beaches or summer destinations across the United States without running into scores of shorts in bright coral, teal, or canary yellow. Thus, pink shorts for men are hardly as elusive as they may have been. Brands like Nautica and even Amazon’s house brand Goodthreads offer their own safe and simplified takes of own pale pink flat front shorts made from a stretch cotton chino material. But seekers of a true mid-century men’s short à la Dickie Greenleaf, complete with elegant pleats from hem to hem and made from a summer-weight fabric? Your search continues.
Dickie sports an extremely casual pair of backless sneakers, appropriately worn sans socks. Despite the four white-laced eyelets, these shoes are meant to be slipped on like sandals and their well-worn white canvas uppers indicate that our favorite profligate makes much use of them over his brunch, beach, and bar lifestyle.
For gents preferring the more traditional shoe with a full back, you can crib Dickie’s aesthetic with the classic Sperry Cloud CVO Deck Sneakers. Backless sneakers are marketed more frequently toward women as these offerings from Keds, Kenneth Cole, and Sturrly suggest.
On his left wrist, Dickie wears his stainless steel watch of unconfirmed make, though online speculation has suggested that it may be a vintage model produced either by Bulova, Hamilton, Longines, or Wittenauer. The wristwatch has a silver dial and is worn on a mesh-like bracelet with the appropriately evocative name of a “Milanese strap,” closing over his wrist with a single-prong buckle.
Dickie adorns both hands with rings, sporting a gold ring with double ridges on the middle finger of his right hand and a flashier gold ring with a green stone that gleams from his left pinky, described as a gift from that Marge that he “had to promise—capital P—never to take it off.”
How to Get the Look
Dickie Greenleaf’s resort-friendly garb should inspire gents to adopt a light and unique summer wardrobe, designed first and foremost for stylish comfort.
- White knit short-sleeve resort shirt with gray mesh-textured chest panels, wide camp collar,
- Pale pink double forward-pleated Bermuda shorts with side adjusters, side pockets, button-through back pockets, and self-cuffed bottoms
- Cream double reverse-pleated trousers with belt loops, straight side pockets, button-through back pockets, and self-cuffed bottoms
- Black leather Gucci belt
- White canvas slip-on backless sneakers
- Steel wristwatch with silver dial on silver Milanese mesh bracelet
- Gold double-ridged ring, worn on right middle finger
- Gold signet pinky ring with green stone, worn on left pinky
The unique shirt would be next to impossible to find, but you can use it as inspiration to discover your own signature summer tops like this retro-influenced Felix Jacquard navy-and-“cloud” pique vintage resort polo shirt by Orlebar Brown.
Do Yourself a Favor and…
I don’t know why people say this country’s civilized!