How Dickie Greenleaf Became a Forever Menswear Icon

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The image is indelible: Jude Law as Dickie Greenleaf in the 1999 film The Talented Mr. Ripley, sporting a half-open knit polo, pleated white shorts, worn-in sneakers, a mischievous smile, and a cigarette dangling from his fingers. It’s so captivating that the picture has seemingly been seared into the brain of every menswear fanatic of the social media age, from elder Millennials to Gen-Z and their fixation on “Old Money” aesthetics. Just look at its frequent appearances on Instagram and TikTok as the Platonic Ideal of how men should dress as proof of its enduring appeal.

While Greenleaf's sartorial influence may live on in perpetuity online, it’s back in the broader zeitgeist, thanks to an eight-part Netflix adaptation titled Ripley starring Andrew Scott in the title role, with Johnny Flynn as Greenleaf Dakota Fanning as his girlfriend Marge. The premise is delicious: Ripley, a mysterious interloper, penetrates a small group of monied flaneurs idling away in Italy, but when his jealousy of their lifestyle grows, he turns violent in order to maintain the glamor of his newfound friends.

The story might resonate no matter what era in which its told, but it’s those costumes that have really left a lingering impression. Take Adam Brown, the designer behind the brand Orlebar Brown which is known for a certain seaside insouciance directly influenced by Ripley’s mid-century Italian Riviera style. “We are all drawn to these rather lost but ultimately charismatic and seemingly always stylish characters,” Brown said. “There is a joy and beauty in Greenleaf’s youth. They are carefree, reckless and extravagant.” Brown recalls the first time he saw the film, when he was serendipitously traveling in Italy, making it the perfect vacation movie. “When we came out of the cinema, I remember we felt a bit frumpy and dowdy,” he recalls. “Not quite living the dream as we had imagined before going in. At that point in my life, I was probably a bit more Ripley than Greenleaf.”

It would be eight years before he launched his own label, which specializes in trim swim trunks and breezy button-downs, but Brown recalls that images from the film were part of his mood board. “He epitomizes Riviera chic with such a clear sense of his place at that particular moment. There is an innate sense of flair which only comes when someone is truly at home or understands their surroundings.” After all, who could forget Ripley's first interaction with Dickie and Marge, them lazing on the beach in tastefully patterned swimming outfits and Ripley in a garish neon-green briefs, an immediate sign that he's not yet learned the sartorial codes of his newfound friends.

“The clothes match their settings perfectly,” he adds. “There’s an authenticity and ease that someone who is trying too hard—like Ripley—can only dream about.”

Textured Stripe Montauk Polo

Cornell Linen Shorts

Short-Sleeve Cashmere Sweater Polo

Intrecciato Leather Espadrille

Textured Stripe Panama Short Sleeve Shirt

Gregory Hand-Tailored Linen Short

Phantos 56mm Round Sunglasses

Ann Roth, the prolific costume designer behind the 1999 film, admits to T&C that she's hazy on some of the particulars of the film—at 92, she has worked on more than 130 projects, with 50 since she worked on Ripley 25 years ago—but did, however, tell the New York Times last year that she considers it her best work and called it her, “fashion piece.”

Today, she says there was some personal resonance at play with the picture: “That was my period,” she says of the era in which the movie is set. “So, it’s just some of the things that I like.”

She also recalls a few things: those blowsy, loose linen shirts were made specifically for Law, because, unlike today, they weren’t an item that was readily available, even at vintage shops. And it was she who insisted that he wear white loafers without socks, though the actor kept asking for a pair. (A funny note: Roth said she’s heard rumors that Gwyneth Paltrow said in an interview she made her own costumes, which is not true; this writer couldn’t find said interview.). Still, Roth isn't on social media and had no idea of the film’s long afterlife, a fact she found amusing.

Jake Woolf, a menswear writer, thinks the film’s enduring interest lies in its ability to walk the fine line between aspirational and achievable. “The core items in menswear haven’t changed all that much since the time of The Talented Mr. Ripley, so I think there’s a valid sense one gets that everything you see on screen is something that can be easily adapted into a wardrobe today,” he says. “That said, even though the setting is casual, things like polos, oxford cloth shirts, and the act of wearing a shirt and tie to lunch have inherently more of a sense of occasion compared to what most are wearing on vacation in 2024, which I think is appealing to a lot of guys who are interested in elevating their style. But ultimately, while very few of us will ever be able to spend entire summers in Italy doing basically whatever we want, we can get a bit of that feeling in our day to day lives by slipping into a knit polo, pair of shorts, loose fitting trousers, or slinky, transparent, short sleeve button-up.”

Indeed, in addition to Orlebar Brown, today there’s no dearth of brands that could help a person evoke their Ripley fantasy (minus murder, one would hope!), Brands ranging from Brunello Cucinelli to J.Crew offer some version of rakish and vacation-ready garments like mid-thigh shorts or linen short-sleeve shirts. And, as Woolf notes, in our exceedingly laid-back times, perhaps Ripley’s magic is more about styling—incorporating a bit of Old World formality to traditionally casual circumstances.

“The styling and mood of the film is utterly timeless,” says Brown, the designer. “Yes, it is from a particular moment in time, but it always feels innately modern. It is a gift that will keep on giving—in another 25 years we will still be having these same conversations about it.”

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