Serpentina
Beauty as a Blessing and a Curse
I meet Lily Dooley in the breaths between life and death. I’m nothing more than a hair on her head. In fragile movements, I trace her neck. In fluid motions, her face deflects. I coil. She clenches. I slither. “Serpentina, open your eyes,” I whisper into her ear. “Come hither. Watch your fears dry up and wither. I can give you the knowledge of good and evil.”
“Your name is Lily? She is Lily, too,” my master reveals. With his meaty hands, he delicately separates one half of my body from the other, wrapped about Mother—she is shining. Her eyes are glass. Her pupils split in two. Into goldens, greens, and blacks! She is cold and unblinking. Bold and constricting. She is Serpentina.
The boa is real. Heavy. Cold. Dooley is being a trooper, as she always is. Just a few days ago, she flew home to Miami after traveling 36 hours from India, and now we are at the Versace Mansion shooting the latest issue of 21 Artistry. When we go to meet the snake handler on the front steps, we are greeted by a bald and burly Russian man in a leather jacket, valet-parking his Harley-Davidson. Dismounting and handing his keys to the valet, Viktor shakes our hands with a smile. His grip is meaty and firm. He towers over us like a statue, but his personality is comforting.
Although nervous at first, five minutes into shooting with the snakes, Dooley is posing with grace and elegance, wearing them like the gold temple jewelry of her Indian ancestors. Between camera flashes, her gaze is stone cold. Suddenly, I’m the statue. I have known her for a long time, but this is not the Dooley I know. She is more calm, confident, and controlled than ever. Her presence demands the attention of the room. Dooley is honing her power without apology. “Instead of becoming more demure, I’m becoming more intense these days,” she says. “I’m done people-pleasing. I’m controlling my own narrative.”
Instead of becoming more demure, I’m becoming more intense these days. I’m done people-pleasing. I’m controlling my own narrative.
Dooley grew up in a peaceful tree-lined suburb in St. Louis, Missouri. Her childhood was shaped by academically rigorous schooling, extracurricular overload, and culturally enriching travel. Like many immigrants, Dooley’s mother Anjali, a first-generation immigrant herself, expected a lot of her daughter for as much as she poured into her. A wildly successful attorney and badass businesswoman, Dooley’s mother was her first idol.
When Dooley wasn’t excelling in school, she was in tennis, dance, cheer, piano, singing lessons, or theater. From the time she was a child, she rarely had a moment of rest. She has always juggled multiple pursuits at once, and to this day, that’s exactly how she likes it.
The thing that made Dooley who she was, however, was her creativity in everything she did. “I always loved all things creative,” she says. “My parents thought I was going to art school. If you look back at my childhood drawings, they were surprisingly good. I’ve always been interested in photography and interior design. I grew up obsessed with HGTV. Bob Ross was my go-to when I was a child. It was one of the only stations available at my grandma’s house.”
Dooley’s childhood creativity was perhaps most evident in her early sense of fashion, which she credits to her mother. “People ask how I became this way. Anjali Dooley is my mother. I grew up stealing from her closet,” she says. “My first fit was from freakin’ Barneys. You know that quote, ‘They were given a silver spoon’? I literally was born with a Tiffany silver spoon in my mouth. My first bikini was from Juicy Couture. I was destined to be this way. I have always been interested in clothing. My mom used to style me. She always had the best outfits and accessories. I grew up in that environment, and I decided to develop my own style with age. I think it was third grade when I said, ‘Mom, I can dress myself now.’”
Dooley grew up living between worlds. Her parents divorced when she was young, and she grew up moving between them, both literally and metaphorically. The firstborn daughter of a white father and brown mother, she often felt conflicted about her biracial and multicultural identity. “I loved and hated it growing up,” she says. “Now I solely love it. It’s hard to come from two different backgrounds. There was a kid in my class who called me a terrorist at my first high school party. I struggled. I didn’t feel Indian enough around Indian people, especially the older generations. Although I felt white enough, a lot of white people felt comfortable making racist comments around me. Sometimes, they still do.”
Starting in fifth grade, Dooley attended Mary Institute and Saint Louis Country Day School, one of St. Louis’s most elite private schools. She earned near-perfect grades, served as cheer team captain, and held leadership roles in student council. On paper, everything looked perfect. At the same time, her personal life was falling apart. She had falling-outs with numerous friends and a toxic relationship that became fodder for what felt like everyone our age in St. Louis during the COVID-19 pandemic.
This is when I became aware of Dooley—when she started telling her side of the story. A senior in high school at the time, I remember watching my peers’ private Snapchat stories tearing her apart. I remember her TikToks, in which she unapologetically defended herself (with receipts), in disbelief. I remember feeling for her, and at the same time thinking, This girl has star power. We joke about it now. “What did I do in high school? I wreaked havoc,” she says. “I was violently mentally ill and was kind of insane, but it was because of the people around me.”
Following high school, Dooley began attending Indiana University Bloomington, pursuing a psychology major and marketing minor. While she thought college would be a fresh start, it turned out to be more of the same. “At Indiana, I was cripplingly anxious,” she says. I didn’t like it after first semester, and I was thinking of transferring. I joined a sorority. Everyone told me it would make things better. I ended up becoming social chair. I felt like when I was there, no matter what I did, I was always in the wrong. I used to get publicly dogged on, so that was sick. Everything that could’ve gone wrong went wrong. Having 150 girls depend on me really stressed me out, and living in the house was not for the weak. Then my guy best friend assaulted me. I went home for a week and a half, and my parents didn’t want me to go back. It was a dark time.”
Despite her friends’ pleas for her to stay, Dooley did what was best for her and made the brave decision to transfer, which is how she ended up at the University of Miami in August 2023. “My transfer process was different from most. I wasn’t entirely sure where I wanted to be, but I knew I wanted to be in a city. I was at a frat formal, and my friend texted me and said, ‘I got into UMiami. Can you just apply, please?’ I looked, and it was the last day I could apply. A couple of mimosas deep, I wrote the supplemental essay, and I got in.”
In Miami, Dooley has thrived more than she ever did in St. Louis or Bloomington. She has built an entirely new life in Brickell—new friends, modeling opportunities, social media work, and this semester, graduation from her dream school. During my spring break, I visited to see it for myself. We spent the week relaxing on the beach, eating amazing food, and, obviously, doing a few photoshoots. I’m pleased to report that while she’s mastered driving Ferraris, her Missouri roots still show; she can handle a horse just as well.
It’s 2025—the Year of the Snake in the Chinese zodiac, a time often associated with wisdom, transformation, and strength. As we prepare to shoot this month’s 21 Artistry issue in the former Versace Mansion, Versace and fashion at large are in a very transformative place.
Days ago, Donatella Versace stepped down as the creative director of the Italian brand after nearly thirty years, naming Dario Vitale as her heir, and taking on a new brand ambassador role focused on philanthropic and charitable work. Vitale, the former design director of Miu Miu, boasts a strong résumé, though he remains relatively unknown to the public. He inherits one of fashion’s most formidable legacies.
Donatella took over Versace after her brother’s tragic passing in 1997. In her time, she has overseen hundreds of fashion campaigns for the brand, while also designing hotels and cars. She has brought Versace into the 21st century with grace and flair and has been a staunch champion for women and LGBTQ+ rights. “Fashion is a weapon that you can use when you need it,” she told us. For the first time since the brand’s inception, a Versace is not at the helm of Versace.
We enter the villa—or as we call it, Dooley’s “MTV crib”—and the concierge leads us to the Aviary Suite. Stepping into the room feels like entering a jungle. The suite is thick, humid, and alive. Parrots, hummingbirds, and doves decorate every corner of the walls. There’s even a cardinal to remind us of home.
Upon arrival, we venture to the roof to catch the last shots before golden hour fades into sunset. Dooley is wearing a Versace Greca border one-piece swimsuit and the Medusa Biggie cat-eye sunglasses Sabrina Carpenter wore in a recent campaign. Miami Beach and Ocean Drive paint the perfect backdrop. I instruct her to pick up one of the shower hoses lining the balcony railings. She turns it on and holds it like a microphone.
As the shutter clicks, Dooley transforms. The golden light pours over her. The sky is ablaze. The image catches flame. The work reveals itself to me. Afterward, we both agree this is a once-in-a-lifetime shot. “Versace stands out to me as a brand because it’s rebellious,” Dooley says. “Their designs are avant-garde and break the traditional rules of fashion. A lot of people think Versace can be too much. They’re not quiet luxury. A Versace woman is not meant to be subtle.”
“It feels unsettling knowing that Gianni Versace’s life was taken on this property,” Dooley continues. “He was so revolutionary in everything he did. Donatella is a fashion diva. She’s everything I’ve ever wanted to be. She’s literally her. It is inspiring to be in a place this historic, where so many powerful people have been, including Donatella herself. She embodies raw confidence.”
When Dooley and I take a break from shooting, she goes to the master bathroom to clean our phones with rubbing alcohol. A bit of a germaphobe myself, I appreciate the gesture, even if this is the tenth time this week. When she returns from the bathroom, she plops down on the couch with me to “audit” each other’s Instagrams. We exchange sanitized phones. I scroll to the bottom of her archived posts. I’m amazed to find a fourteen-year-old Dooley posing in a white T-shirt and jeans in a photography studio. “This needs to be unarchived. This is so iconic. What?” I say, clicking “Show on profile.”
“When I was fourteen, a guy approached me at Starbucks and asked if I was interested in modeling,” she says. “My mom met him with me and sniffed him out. She handles all my affairs. I never really did anything with it. My mom didn’t want me spending my high school and college years modeling. She always thought it was vain. In our society, I understand where she’s coming from. She wants to protect me, but I can’t let other people’s projections—especially men’s—dictate my choices.”
I can’t let other people’s projections—especially men’s—dictate my choices.
Viktor, the snake handler, texts Dooley that he’s here, and we go downstairs to meet him. He unzips his backpack and pulls out two boa constrictors, one of them also named Lily. At first, Dooley shakes in fear. When placed on her shoulders, the albino boa constrictor that looks straight out of Britney Spears’s classic “I’m a Slave 4 U” performance, does what it was born to do: constricts. Even as the snake tightens around her, Dooley is careful to be gentle with the animals. Although I often joke that I hate TikTok language, I know it resonates. I tell her, “Lock in.” She nods. It doesn’t take long for her to transform into a sorceress of mythic proportions. She is fierce, commanding, and powerful. I am petrified.
The Medusa head is the iconic emblem of Versace, chosen by Gianni Versace himself for its symbolism of power, seduction, and mythology. Medusa, before she became a monster, was a mortal woman, once considered the most beautiful in all of Greece. According to myth, she was raped by Poseidon in Athena’s temple. As punishment—not for the act, but for desecrating the sacred space—Athena cursed her, turning her hair into snakes and her eyes into weapons. She was punished not for what she did, but for what was done to her. That is the story of so many women.
“Society hates sexual women,” Dooley says. “People think that just because a girl is pretty, she benefits a lot. In reality, women are valued for their appearance more than anything they can offer of substance. I wonder if I’m valued for who I am or if it’s how I look. It gives me impostor syndrome. In weak moments, I wonder if I’m supposed to be here. It makes me feel unsafe sometimes, especially in a place like Miami. There’s pressure to look good all the time, but if you do look good, you’re constantly put in situations where people feel entitled to your time or even your body. It’s the most conditional shit in the world. Your looks are going to fade with time.”
“People assume you’re superficial, vain, or stupid. I feel like I’m not taken seriously in relationships, both platonic and romantic. People put me on a pedestal, and it takes getting to know me more for them to realize I’m a human, and then I lose value. People think your life is so easy, and if you complain about anything, people either don’t believe you, don’t listen to you, or resent you. It’s hard to get genuine empathy sometimes. People sarcastically say, ‘Your life must be so hard.’ You don’t know even a morsel of the shit I’ve been through.”
After the snake portion of the shoot concludes, Dooley and I walk across the street for sushi and gelato. We discuss art, life, and our plans for the summer. We arrive back just in time for Jacquelyn Todd, Dooley’s former freshman-year roommate, to join us. Like me, she is also in town for spring break. Over the years, I have heard stories about Todd and their iconic sisterhood. Dooley has always said the hardest part of leaving IU was leaving her best friend. “As Lily’s long-distance best friend, it has been a privilege to watch her flourish and find her place,” Todd says. “Seeing her choose to leave a place that no longer served her was truly inspiring and speaks to her fearlessness, confidence, and spontaneity. Lily is always doing something new to challenge herself, and she is always hustling. I’ve always known she would go far.”
Once Todd gets settled, we walk back out onto Ocean Drive in search of ingredients for her famous Aperol Spritz. On our fifteen-minute freezing-cold walk to I Love Liquor, we joke about wishing we’d Ubered, agree that the numerous prostitutes we pass are iconic, and formulate plans to get drunk in the Million Mosaic Pool after the shoot is over.
The styling for the next look was inspired by Lady Gaga’s 2018 appearance at the 25th annual Women in Hollywood celebration, where she delivered a powerful speech on surviving sexual assault and mental health. “In this suit, I felt the truth of who I am well up in my gut,” Gaga said. “And then, wondering what I wanted to say tonight became very clear to me. As a sexual assault survivor by someone in the entertainment industry, as a woman who is still not brave enough to say his name, as a woman who lives with chronic pain, as a woman who was conditioned at a very young age to listen to what men told me to do, I decided today I wanted to take the power back. Today, I wear pants. Today, I wear the suit.”
The second floor of the Versace Mansion is a testament to Gianni Versace’s passion for classical antiquity and his desire to intertwine art, history, and personal expression. Originally constructed in 1930 by Standard Oil heir Alden Freeman, the villa was inspired by the Alcázar de Colón in Santo Domingo, the residence of Diego Columbus, son of Christopher Columbus. Freeman adorned the property with over 100 medallions depicting notable historical figures, including Lenin, Mussolini, and Julius Caesar, reflecting his eclectic interests and the political climate of the era.
Holding an Aperol Spritz made by Todd, Dooley poses in an oversized men’s Calvin Klein suit and men’s Tom Ford sunglasses in front of these influential male figures of history. “I felt uneasy at first, because I have never worn a suit, but it was more comfortable than I expected,” Dooley reflects. “I’m reclaiming my power. Girls are always expected to dress a certain way to impress men and submit to the male gaze. It’s empowering to reclaim that and wear the pants—literally. I really cannot be friends with a male-centered bitch. It irks me to no end. You have no self-respect if you’re a male-centered person. I just don’t relate to them, truly.”
“You think a male-centered girl is kind of inconsequential,” Dooley continues. “But prioritizing men in a society where men are already that valued—and prioritizing what they think, what they want, their opinions over your own—that may seem small, but it’s the most negative thing you can do to a woman’s potential. You’re basing your entire existence on what men think of you, and that’s such a sad way to live. A lot of men don’t even have respect for themselves. You want validation from that? Why would you prioritize him being comfortable and his needs over your own?”
The suit marks the final look from the shoot, and we make our way to the pool with our Aperol Spritzes. Todd deserves full credit: they are some of the best drinks I’ve ever had. “We’re gonna go spring breakers!” I joke, referencing the Kesha remix of the Charli xcx song that just dropped. We end up not getting very drunk since we’re not allowed to have glasses in the pool. It’s probably for the best, because I was already drunk for most of the shoot. Oops.
The next morning, we wake to a beautiful breakfast spread brought to our room. What can I say? We wanted to feel like Ariana Grande, Doja Cat, and Megan Thee Stallion in the 34+35 Remix music video. We joke about our haters and the people who have wronged us. Some people deserve to be laughed about. “My mom has taught me many things throughout my life,” Dooley says. “One of the things she taught me was that for someone to claim defamation of character and even begin to sue, you must prove beyond all reasonable doubt that what they’re saying was false and caused some sort of loss. The thing is, everything I’ve said publicly about people who have wronged me has been true. I never signed an NDA. I can say whatever I want, and I never say who it’s about. People are figuring it out of their own volition. That’s not on me. If you do bad things, I’m going to tell people. Actions have consequences. As Taylor Swift said, ‘If guys don’t want me to write bad songs about them, then they shouldn’t do bad things.’”
Speaking of Taylor Swift, it has become clear to me that Dooley is in her Reputation era. In Swift’s 2017 album, the snake became a reclaimed symbol—from insult to empowerment. Dooley too has learned to let perception work in her favor. “I’ve never really defended myself,” she says. “When Taylor experienced that scrutiny at the hands of a powerful man, she didn’t rush to defend herself. She let her work speak for itself. That’s why I love hanging out with you. You remind me I should be doing things because I want to, not because it makes me more palatable for other people.”
Donatella Versace famously said, “Creativity comes from a conflict of ideas.” For a woman like Dooley, beauty doesn’t mean just one thing. It is layered, complex, and changes over time. Serpentina is not one woman. She’s every woman who’s ever been called too much, too sharp, too loud, or too in control.
Serpentina is elegance with teeth. She moves like myth. She sheds what no longer serves her, just as a snake sheds its skin. She is soft until she strikes.
Beauty is power wrapped in beautiful packaging. People either worship it, fear it, or try to control it.
“Beauty is both a blessing and a curse, while also being quite literally the least interesting thing about me,” Dooley says. “Beauty is power wrapped in beautiful packaging. People either worship it, fear it, or try to control it. For every genuine compliment I’ve ever received, I’ve received a million compliments masked in assumptions, projections, or jealousy, sometimes even in expectations I never asked for. Men tell me they don’t deserve me or aren’t good enough for me the second they realize I’m a real human with real feelings. I’m supposed to be happy or grateful just to be seen. I will never again make myself feel small to make someone else feel big, especially not a man.”
The story of Medusa is familiar because women still live it every day. Medusa was made into a monster for surviving.
She didn’t hide; she stared back. She flipped the gaze. She dared to ask the question, “What if being looked at isn’t vulnerability, but a threat?”
Dooley has learned to see beauty and womanhood not as weaknesses, but as sources of power. She has never once backed down from what was meant to break her, even in the hardest times, and through that fearlessness, she has dared to defy and subvert the expectations placed on women since the beginning of time.
As Lady Macbeth once advised, “Look like the innocent flower, but be the serpent under’t.” •
Editorial
Photography: Philip Hiblovic
Creative Direction: Philip Hiblovic & Lily Dooley
Styling: Philip Hiblovic & Lily Dooley
Hair: Philip Hiblovic & Lily Dooley
Makeup: Philip Hiblovic & Lily Dooley
Location: Versace Mansion
Production
Editor-in-Chief: Philip Hiblovic
Executive Producer: Philip Hiblovic
Story: Philip Hiblovic
Interview: Philip Hiblovic
Layout: Philip Hiblovic
Publisher: Philip Hiblovic
Fashion
1 │ Aviary Suite
Retrofête dress
2 │ Onyx Bar
Toccin dress; Presleys Pumps
3 │ Terrace & Million Mosaic Pool
Versace swimsuit & sunglasses
4 │ Second Floor
Calvin Klein suit; Tom Ford sunglasses; Jennifer Miller necklace
5 │ Upper Rotunda
Vintage dress; Michael Kors sandals
