Fashion knows her face and you already know her name, but with Love Story, she embarks on an alluring new chapter in a storied family tree
Words by CHRISTINE LENNON
Photography by EMMAN MONTALVAN
Styling by CHRISTOPHER CAMPBELL
“It’s the first time most people have registered that I’m acting, even though I’ve been doing it a long time.”
It’s fun to watch people spot Dree Hemingway out and about in L.A., ordering coffee in Hollywood on a Wednesday morning. The 38-year-old actor, model, and mom of a 3-year-old girl is clearly someone. She has what you’d call presence, and bone structure that practically demands to be photographed. Strangers consider her face for a few seconds, puzzling over where and when they’ve seen her. It has been this way for Hemingway for the nearly two decades she’s been working in front of the camera. She’s carried her heavyweight last name and legacy as Mariel’s daughter and Ernest’s great-granddaughter lightly, making a living as a model, establishing her acting career with intriguing parts in indie movies, and flying just under the radar.
But then Ryan Murphy’s smash hit Love Story happened earlier this year, and a seismic shift is now in progress.
“This show was my first adventure into television land after working mostly in independent film. So it’s the first time most people have registered that I’m acting, even though I’ve been doing it for a really long time,” says Hemingway, who portrayed Daryl Hannah, the actor and former girlfriend of John F. Kennedy Jr. To look at her today — wearing no jewelry except a wedding band, a plain white T-shirt, perfectly aged denim, and a navy crewneck tied around her shoulders — it seems she could have played a convincing Carolyn Bessette Kennedy too. From the friendships she made on set with fellow phenoms Paul Kelly, Sarah Pidgeon, and Grace Gummer, to the chance to revisit her carefree life in New York in her 20s, the experience has been a game changer.
“Paul reminded me that we worked together on a Tamara Mellon campaign for Jimmy Choo years ago, and it was incredible to work with him again,” she says. “Grace is like family. Sarah is just a magical creature. There were no big egos.” The nine-episode show racked up more than 65 million viewing hours by its conclusion, setting a record for Hulu/Disney+ as its most watched FX series. Vintage Calvin Klein searches soared on resale sites (Bessette Kennedy worked for the designer); across TikTok and Instagram, there was a posting frenzy of “what we looked like in the 1990s.” But some living members of the Kennedy family, as well as Hannah, dismissed the show.
The writer Derek Blasberg jumped to its defense in his And Another Thing Substack newsletter. “I loved Dree Hemingway’s performance so much I went back and watched old interviews of Hannah on The Tonight Show with Jay Leno — she nailed the giggle, the cadence, the whole thing,” he wrote.
“It was incredible, and I am so grateful,” Hemingway says. “I mean, there’s part of me that wishes it had happened earlier. Obviously I have that female fear of aging. So I worry about time, but I feel more comfortable with myself than ever.”
Getting to this place — as a performer and a person at ease with the space she and her family occupy in contemporary American culture — has taken some effort. The work has paid off, as demonstrated by the way Hemingway discusses her atypical background with clarity and candor — including growing up knowing of her mother’s talent and fame, as well as the tragedy and mental health challenges previous generations of Hemingways faced. “My ’90s were spent wearing Old Navy, with my very long, unbrushed hair, mildly albino, talking to animals,” she says, laughing. “I was outside constantly.”
After her mother, Mariel, had a blaze of fame and glory in her early life — starring in cultural lightning rod movies like Personal Best and Star 80, and earning an Academy Award nomination for Woody Allen’s Manhattan in her teens — she moved back to Sun Valley, Idaho, in the late ’80s to raise her two daughters away from the glare of Hollywood. Hemingway and her sister, artist Langley Fox, just 21 months younger, grew up river rafting, hiking, and watching Nick at Nite and Turner Classic Movies. They weren’t completely removed from the trappings of fame, since they attended Ernest Hemingway Elementary School. The shadow of their great-grandfather, who committed suicide in 1961 three months before Mariel was born, loomed large. And the death of their aunt, Mariel’s sister Margaux, from a drug overdose when Dree was 9 years old contributed to the air of tragedy that clings to the Hemingway family story.
“It was different [in Idaho] because we were little kids. The parents knew, but they wouldn’t talk to us about it,” she says. “When we moved to California when I was in middle school, I started to think about my family differently and understand it — especially when I was asked to read my great-grandfather’s books in high school, and my teachers asked me for inside information that I didn’t have. Now I understand the obsession. But it was almost embarrassing then. Historians and English majors know more about him than I do. But it is fascinating. I did go through a period when I was younger when I rebelled against it. I was angry that people wanted me to know about him, for some reason.” She laughs. “And now I’ve matured.”
Hemingway credits Mariel’s commitment to mental health education for giving her the tools and perspective to handle the pressures of growing up as part of that dynasty. Her mother founded the Mariel Hemingway Foundation and is a prominent mental health advocate, author, filmmaker, and speaker who works to destigmatize mental illness, suicide, and addiction.
“My mom has always been my inspiration,” she says. “She tried very hard to give us a normal upbringing, and she very much sheltered us from the hoopla of it all. But that’s all I’ve ever known. I’ve been put on a pedestal, which in some ways I like because I’m a performer, and I like being the center of attention. But then because of that pedestal, people sometimes forgot I was also going through the same things everyone else goes through.”
“Obviously I have that female fear of aging. So I worry about time, but I feel more comfortable with myself than ever.”
As a fiercely independent teen who knew she wanted to pursue a career in acting, she left school early, earning a GED diploma, and quickly became an in-demand model, working for brands including Chanel, Gucci, Valentino, and Chloé. Her sister also modeled to support her art career, and they’ve both grown to appreciate the privilege more than they did in their younger years.
“Being a starving artist is hard, and we both have modeled mainly to pay the bills,” she says. “I’m really grateful that fashion has supported me, and I haven’t just done it for money exclusively. You do have those jobs where you feel like a prop, which I used to dislike. I have started to love it, though. I enjoy taking pictures more because I’m not comparing myself to what the standard is. Maybe after having a kid, I don’t take so many things as seriously.”
All the while, she has had movie roles, appearing in festival favorites like Sean Baker’s Starlet in 2012, which the Oscar winner made early in his career. Hemingway’s performance earned praise for her charm and sensitivity in portraying an adult film star. “That film was such an adventure. It was independent but really guerilla, with hidden cameras and a lot of improv,” she says. “There was so much exploration and trust involved.”
Today Hemingway and her Italian partner, Nick Delli Santi, split their time between their home in West Hollywood and an apartment in Rome. She is trying to piece together a childhood for her daughter with some access to nature and open spaces, as she had, but with closer proximity to the business. Fortunately, the Hemingway legacy doesn’t faze Delli Santi. “It’s not something that he thinks about. I’m a big character to begin with, and very much the focal point of the relationship,” she says, laughing. “I can see it sometimes with our larger community, when people introduce me as Ernest Hemingway’s great-granddaughter. I think, ‘Oh, I see what’s going on here.’ I understand. It’s exciting for them, and I don’t want to take that away from them. I’m OK with it. And he doesn’t care. He’s great.”
She’s preparing for another movie role, but she’s tight-lipped about the details. And her days as a vaguely familiar but underrecognized face appear to be numbered. “The director of this project called me and said, ‘You’d better stay pale,’ which will be hard, since I was just outside so much this weekend for my daughter’s third birthday party,” she says. It’s hard to picture Hemingway hiding in the shade. With her classic good looks, her down-to-earth charm, and her relaxed nature, she’s the very picture of the Golden State.
“I’m like the poster child, I know. I’m a very sunny person,” she says. “I can’t help it.”
Shot on location at Lotusland, Montecito’s sprawling botanical gardens where rare plants join all manner of flora. Lotusland Celebrates, the nonprofit’s annual gala, will be held July 18. The afternoon-to-sunset event, which benefits the organization’s mission to preserve the natural world — complete with a garden walk, dinner, and live auction — will be hosted by Jane Lynch with special guest Martha Stewart. Code LOTUSLAND10 for a virtual trunk show with premier partner Oscar de la Renta benefits the Gardens. Also on offer are lots including a garden tour and lunch with Stewart at her Bedford estate, a Rose Story Farm bespoke garden design, David Webb jewelry paired with a New York experience, and a stay at Château Troplong Mondot with a Bordeaux tasting and Michelin-starred dinner, among many others. Online auction July 9–19, lotuslandcelebrates.org.
Hair by TAKUYA SUGAWARA using Bumble & Bumble at Walter Schupfer.
Makeup by TOBI HENNEY at The Wall Group.
Manicure by ALEX JACHNO at Opus Beauty.
Prop styling by PETER GUERACAGUE.
Shot on location at GANNA WALSKA LOTUSLAND in Montecito.
Feature image: PRADA dress, price upon request, shoes, $1,290, and bag, $4,400. Headscarves worn throughout, stylist’s own.
This story originally appeared in the Fashionable Living 2026 issue of C Magazine.
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