Dree Hemingway’s Hollywood Dream Comes True

After a string of indie hits the model turned actor is a bona fide film star

Photography by CURTIS BUCHANAN
Fashion Direction by PETRA FLANNERY



It’s a warm summer morning in the blooming garden of Dree Hemingway’s vine-covered post-war home in Laurel Canyon, and she wants to talk about perception versus reality. “It’s funny, because I [have] always felt like I’ve had impostor syndrome while modeling. I’ve never felt like a model.” She knows how that sounds; her delicate bone structure, glacial blue eyes and lithe frame have brought her countless campaigns, editorials and catwalk opportunities. Inarguably, she was and is a very good model. But that’s perception talking. “I was just at therapy, and I was talking about how I’d recently done a lot of photo shoots and came off a movie, and I realized I love acting way more than I love taking photos,” she says. “On a photo shoot, people create their perception of who you are, and they want you, but the you that they think you are. And the me that I am”—a blonde and willowy self-professed “whack-job nerd” who has spent the past few days staying up late watching all of Star Wars in chronological order—“is something only I can feel or know.” She tugs at a vape pen. “I’ve also struggled with the fact that the only reason people want me is because I’m a Hemingway. It’s made me want to prove myself even more.”

Hemingway—yes, her great-grandfather was Ernest, author of The Old Man and the Sea, and her mother is Mariel, of Manhattan fame—made her runway debut for Givenchy at Paris Fashion Week in 2009. She has been steadily working at the upper tier of modeling ever since, appearing in campaigns for the likes of Chanel, Gucci, Valentino and Paco Rabanne while slipping out to star in indie films like Sean Baker’s 2012 Independent Spirit Award-winning Starlet. (The New York Times called her “a spectacular find.”) More recently she’s turned up playing a string of bewitching hipsters in projects helmed by a regular who’s who of indie darlings: Alex Ross Perry’s Listen Up Philip; Noah Baumbach’s While We’re Young alongside Ben Stiller, Adam Driver and Amanda Seyfried; and Michelle Morgan’s It Happened in L.A.


RODARTE dress, $2,200, and sweater, $1,335.


DIOR shirt, skirt, corset, boots, earrings and ring (left), prices upon request. CARTIER ring, $2,520.


BOTTEGA VENETA dress and sweater, prices upon request.


Part of the appeal of acting over modeling lies in its challenges. “[Acting is] not just about being pretty or fitting into the clothes,” Hemingway says. “I’m also almost 35 and don’t fully fit into the clothes anymore, which is wild, but that was a thing in my 20s, a big thing for me, needing to fit into the clothes. I’m a lot healthier than I was then, and I’m a lot more grown-up. Sometimes going into photo shoots can trigger me into thinking that I’m not good enough.” She pauses to pat her dog, Bear, a 2-year-old rescue with fluffy haunches who has been patrolling the perimeter. “I shouldn’t be complaining about modeling because it’s delightful, but I just want to be making films.”


“I always felt like I had impostor syndrome. I never felt like a model”

dree hemingway


Hemingway recently wrapped The Kill Room in New York with director Nicol Paone. The dark comedy/thriller skewers the art world and stars Uma Thurman and Samuel L. Jackson. Hemingway and Thurman play competing New York gallerists, while Jackson plays a gangster whose money-laundering scheme accidentally turns his hit man (Joe Manganiello) into a contemporary art-scene sensation. Thurman’s daughter and former C cover star Maya Hawke is also in the cast. “It’s a really, really fun film,” says Hemingway.

Hemingway grew up in Ketchum, Idaho, with her actor mother, her father (television documentarian Stephen Crisman), and her younger sister, Langley Fox (now an artist and model), before moving to Thousand Oaks for her high school years. Her experience introduced her to a type of adolescence that she says she drew on while creating her character for Starlet, an adult film actor who is stuck in a rut and searching for something more. One would think such a girl would be excited to have a Hemingway in her class. “The girls I knew growing up were very competitive,” Hemingway says. “I never fully felt like I fit in.”


HERMÈS dress, $11,900. POMELLATO earrings, $2,500, and bracelet, $21,200.


At home, television wasn’t allowed, except for anything on the Turner Classic Movies channel. “I became obsessed with Old Hollywood. To Catch a Thief and anything with Katherine Hepburn.” She would visit her mother on set and learned to love the team-sport aspect of making movies. “My mom said you can do anything when you turn 18. And one thing she said is, ‘I never want to hear that you’re a bitch; I will pull you out of there so fast.’ And so my thing is showing up on set, whether I’m in a really bratty mood or something’s happened that’s triggered me, I bring some light or festivity with me.”

Hemingway divides her time between the east and west coasts, and when she is not at her tranquil canyon perch overlooking Los Angeles, she rents a room from a friend in New York. Recently engaged, she met her fiancé, Nick Delli Santi, in L.A. and shows off an elegant oval-shaped diamond trimmed in a halo of small round-cut diamonds on a thin band of his design. “He did good!” she says. Is he a jewelry designer? “No! He works in real estate,” she laughs. “I was really shocked by how good the ring was. I always thought, like, if I get a bad ring, is this not my person because he doesn’t know me?”

At top of mind these days is a new film shooting in September, one that she isn’t quite ready to discuss. So, for now, wedding planning is taking a back seat. “I’ve always had the dream of a family and kids, but I’ve never pre-thought out my wedding. I’m terrified of becoming a monster bride … what do they call it? A bridezilla. That terrifies me.” Hemingway suspects the only person she’ll call in for bridesmaid duty is her sister, who also lives in L.A. “She’s my best friend.”


CHANEL dress, $7,300, cardigan, $5,250, belt, $1,375, and necklace, $2,100. CARTIER rings, from $2,520.


SAINT LAURENT by ANTHONY VACCARELLO dress, $5,490, bracelets, from $1,090, and sandals (not worn), $1,150. ADIDAS sneakers, $80.


GIORGIO ARMANI top, $7,400, pants, $1,359, and coat, price upon request.


BRUNELLO CUCINELLI cardigan, $3,700, and skirt, $8,895.


At least the location is likely set. “My fiancé is from Rome, so we’ll probably get married there,” she says. “The only thing I’m concerned about is the dress.” A great perk of being a fashion favorite can also be a pitfall, and the crowd can be sensitive: “I have so many friends who are designers, I almost want to find a vintage one to not even go down that road.” In fact, not letting herself get weighed down by other people’s emotions and expectations around the big day might be the biggest hurdle of all. “My whole thing about a wedding is I don’t want someone to feel left out if they’re not invited. It’s more so about the other people than myself, and then that gives me anxiety.”

After two-plus years of quarantining and self-actualization, has Hemingway’s own style changed? “I’ve definitely moved past my 20s, where I was like, ‘Woo! I wanna look like that,’ to where I’m just very simple,” she says. “I pretty much just want to wear The Row all the time and mix in Pop-y aspects. Really not a lot has changed. I think my hormones dictate a lot of things. I’ve matured. I’m more stable.” In the past, however, she experimented with her look in other ways, such as when she shaved her head for a role in 2018. “I’m so glad I did it, because I used to hide behind my hair as a security blanket. I couldn’t hide from anything.” She was surprised to find women were suddenly far more open to her, too. “I made a lot of girlfriends with the buzzed head,” she says. “I’ve always had a harder time with girls.” But maybe that was just her perception. She’s more than ready for her new reality.


Hair by HOLLY MILLS at The Wall Group.
Makeup by GINA BROOKE at The Wall Group.
Manicure by EME KUDO at Opus Beauty using DIOR Vernis.


Dree Hemingway wears MIU MIU dress, POMELLATO earrings (on left ear) and CARTIER ring.



Feature image: PRADA top, $995, and skirt, $3,500. BULGARI ring, $12,600.


This story originally appeared in the Fall 2022 issue of C Magazine.

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