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.

MODERN MEDUSA  She no longer runs from the gaze. She commands it. Dooley reclines not as prey, but as prophecy — beauty, danger, and rebirth coiled into one. Retrofête dress.

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 this month’s 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 wearing a leather jacket valet parking his Harley Davidson. Dismounting and handing his keys to the valet, Viktor shakes our hands with a smile on his face. His hands are 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 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 with no 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.”

Dooley grew up in a peaceful tree-lined suburb in St. Louis, Missouri, close to the city, yet quietly tucked away from its chaos. Her childhood consisted of academically rigorous schooling, holistic extracurricular activities, 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 and gave her big shoes to fill, probably Christian Louboutin heels to be specific. She always rose to the occasion. When Dooley wasn’t excelling in school, she participated in tennis, dance, track, cheer, piano, singing lessons, and 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 shares. “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.”

DRAPED IN MYTH  Retrofête dress.

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 recalls. “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’s just the coolest human ever. She always had the best outfits and accessories. I grew up in that environment, and I decided to have my own style with age. I think it was third grade when I said, ‘Mom, I can dress myself now.’”

Dooley’s upbringing wasn’t always positive. Her parents divorced at a young age, and she grew up living between them, literally and metaphorically. The firstborn daughter of a white father and Indian mother, she felt conflicted about her biracial and multicultural identity. “I loved and hated it growing up,” she shares. “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, and although I definitely felt white enough, a lot of white people felt comfortable enough around me to make racist comments, and they still do, which I don’t condone.”

FASHION WITH FANGS  “Instead of becoming more demure, I’m becoming more intense these days. I’m done people pleasing. I’m controlling my own narrative.”

Starting in fifth grade, Dooley attended Mary Institute and Saint Louis Country Day School (MICDS), a private, coeducational college preparatory school located on a 110-acre campus in Ladue, Missouri, ranked the #1 K–12 school in the state. While at MICDS, Dooley experienced ups and downs. She earned near-perfect grades, served as cheer team captain, and held a leadership position in student council. 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 the public opinion of what seemed 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 a continuation of the same horrors she endured in high school. “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. Sophomore year was hell. 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.”

THE ART OF CONTRAST  Zebras have long been a symbol of duality. They symbolize individuality and nonconformity. Toccin dress and Presleys Pumps heels.

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 the rest. 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 Julia Ford, who has become more like a sister, texted me and said, ‘I got into UMiami. Can you just apply please?’ I looked, and it was the last day I could’ve applied. A couple mimosas deep, I wrote the supplemental essay about why UMiami, and I got in.”

In Miami, Dooley has thrived more than she ever did in St. Louis or Bloomington, and as her friend, it has been a joy to see. She has built a whole new life in Brickell without missing a beat. She has made countless new friends, pursued modeling and social media opportunities, and is graduating from her dream school this semester. During my spring break, I visited to see what all the fuss is about. 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.

UNTAMED GLAMOUR  Toccin dress.

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, crowning Dario Vitale as her heir, and taking on a new brand ambassador role focused on philanthropic and charitable work. The former design director for Miu Miu, Vitale, boasts a strong resume, although he is still relatively unknown to the public. He has big shoes to fill. Donatella took over Versace when her brother tragically passed away in 1997. In her time, she has overseen hundreds of fashion campaigns for the brand, also designing hotels and cars. She has brought Versace into the 21st century with grace and flair. Donatella has also been a staunch champion for women and LGBTQIA+ rights. “Fashion is a weapon that you can use when you need it,” she told us. This will be the first time since the brand’s inception that a Versace is not at the helm of Versace.

We enter the villa, or as we call it, Dooley’s “MTV crib,” and we are led to the Aviary Suite. Stepping into the room feels like entering a jungle—thick, humid, alive. Parrots, hummingbirds, and doves decorate every corner of the walls. Upon arrival, we venture to the roof to catch the last photo opportunities before the end of golden hour and the beginning of 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 paints the perfect background. 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. Through the photography and the fashion, she tells her story. The golden light pours over her. The sky is ablaze. The image catches aflame. The work reveals itself to me. Afterwards, we both agree this is a once-in-a-lifetime shot.  “It feels unsettling knowing that Gianni Versace’s life was taken on this property,” Dooley says. “He was so revolutionary and inspiring with 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 deeply historical environment such as this, where so many powerful people have been, including Donatella herself. I was channeling my inner her. She presents raw confidence. Versace stands out to me as a brand because it’s rebellious. Their designs are out there 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’s fashion uplifts her self-confidence, not to be seductive or for the male gaze, but for herself.”

GOLDEN HOUR  Dooley poses on the Versace Mansion roof with Miami Beach behind her. Versace swimsuit and sunglasses.

When Dooley and I take a break from shooting, she goes to the master bathroom to clean our phones with rubbing alcohol. Being a bit of a germaphobe myself, I appreciate the gesture, even after 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. When it’s her turn, I scroll to the bottom of her archived posts. I’m amazed to see 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 he asked if I was interested in modeling,” she says. “He gave me his card. 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 to spend my high school and college years modeling. She always thought it was kind of vain. In this society, I understand where she’s coming from. She wants to protect me, but I can’t let other people’s projections, mostly men’s, dictate my choices.”

Viktor, the snake handler, texts Lily that he’s here, and we go downstairs to meet him. He unzips his backpack and pulls out two boa constrictors, one named Lily. At first, Dooley shakes in fear. The albino boa constrictor that looks straight out of Britney Spears’s classic “I’m a Slave 4 U” performance, placed on her shoulders, does what it was born to do: constricts. Even as she gets choked by the snake, Dooley goes out of her way to be gentle and caring of 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.

MIAMI HEAT  Versace swimsuit and sunglasses.

The Medusa head is the iconic emblem of Versace, and it holds deep, deliberate significance, chosen by Gianni Versace himself for its symbolism of power, seduction, and mythology. That duality—being both desired and feared—mirrors the Versace woman: glamorous, unapologetic, and untouchable. 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, her eyes into weapons. She was punished not for what she did, but for what was done to her. That’s the story of so many women. “Beauty is like a curse,” Dooley says. “Society hates sexual women. Medusa is cursed for something that happened to her, not something she did. People think that just because a girl is pretty, she benefits a lot. In reality, they’re valued for their appearance more than anything they can offer of substance. It applies everywhere. You just never get any genuine validation. I wonder if I’m valued for who I am or if it’s because of 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 also assume you’re very superficial, vain, or stupid. I feel like I’m not taken seriously all the time in relationships, both platonic and romantic. People put me on some sort of pedestal, and it takes getting to know me more for people to realize I’m a human, and then I lose value. You lose value when people realize you’re actually a human. 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 or rapport sometimes. People sarcastically say, ‘Your life must be so hard.’ You don’t know even a morsel of the shit I’ve been through.”

 MOSAIC MUSE  Dooley in the Million Mosaic Pool. Versace swimsuit.

After the snake portion of the shoot concludes, Dooley and I walk across the street to grab sushi and gelato. I admittedly start to get tipsy around this time. We discuss art, life, ideas, and our plans for the summer, of which there are many. We arrive back just in time for Jacquelyn Todd, Dooley’s former freshman-year roommate at Indiana University Bloomington, to join us. Like me, she is also in town for spring break. Over the years, I have heard so many 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 Miss Dooley 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. Seeing her pursue modeling just makes sense as she is both stunning on the inside and out. I’m excited for the world to see her beauty. I’ve always known she will go far.”

“Beauty is like a curse. Society hates sexual women. Medusa is cursed for something that happened to her, not something she did. People put me on some sort of pedestal, and it takes getting to know me more for people to realize I’m a human, and then I lose value.”

Once Todd gets settled, we walk back out onto Ocean Drive in search of ingredients for Todd’s famous Aperol Spritz. On our fifteen-minute freezing cold walk to I Love Liquor, we joke about wishing we Ubered, agree the numerous prostitutes we see are iconic, and formulate plans to get drunk in the Million Mosaic Pool after the shoot is over.

SUIT OF ARMOR  “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.”  Calvin Klein suit and Tom Ford sunglasses.

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 mansion 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 wearing 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 thought,” 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.”

TAILORED FOR TAKEOVER  Calvin Klein suit and Tom Ford sunglasses.

Dooley continues, “You think a male-centered girl is kind of inconsequential. But prioritizing men in a society where men are already that valued, and you’re prioritizing what they think, what they want, their opinions over your own—that is the smallest act, but it’s the most negative thing you can do to a woman’s potential. You’re basing your entire existence off 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. I must hand it to Todd: 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 that drunk since we’re not allowed to have glasses in the pool. It’s probably for the best, because I was already drunk for the majority of the shoot. Oops.

 ONE BLOOD  Dooley poses on the wall of the Versace Mansion’s second story, which depicts influential male figures of history. Calvin Klein suit and Tom Ford sunglasses.

The next morning, after a restless night’s sleep, we awake 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 in the past. It’s all in good fun. “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 have to be able to prove beyond all reasonable doubt that what I’m saying was false and led to some sort of loss. The thing is…All the shit I’ve said people who wronged me have done—things I’ve shared publicly—have 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 on their own volition. That’s not on me. If the shoe fits, wear it. 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.’”

“You think a male-centered girl is kind of inconsequential. But prioritizing men in a society where men are already that valued, and you’re prioritizing what they think, what they want, their opinions over your own—that is the smallest act, but it’s the most negative thing you can do to a woman’s potential.”

Speaking of Taylor Swift, it’s become clear to me that Dooley is in her “Reputation era,” a pop culture phrase referencing Swift’s 2017 album in which the snake became a reclaiming symbol, from insult to empowerment. “I’ve never really defended myself,” Dooley 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 it more palatable for other people.”

GOTHIC GODDESS  The styling for this look was inspired by the character Morticia Addams from the Addams Family franchise. Morticia is a symbol of feminine power that doesn’t conform. Michael Kors heels.

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, too in control. She 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 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 twenty 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.”

GAZE FLIPPED  “Beauty is power wrapped in beautiful packaging. People either worship it, fear it, or try to control it.”

Like many women, Medusa was turned into a monster for existing and then feared 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?” As Dooley’s friend and collaborator, it has been a joy to see her hone her beauty and womanhood as the superpower that it is. Dooley has never once backed down from fighting her battles, 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 advised: “Look like the innocent flower, but be the serpent under’t.” •

Photography: Philip Hiblovic

Words and Interview: Philip Hiblovic

Styling: Philip Hiblovic and Lily Dooley

Hair: Philip Hiblovic and Lily Dooley

Makeup: Philip Hiblovic and Lily Dooley

Creative Direction: Philip Hiblovic and Lily Dooley

Production: 21 Artistry

Location: The Villa Casa Casuarina at the Former Versace Mansion

Look 1: Dress by Retrofête; ring, bracelets, and earrings — artist’s own; snakes — courtesy of Snake Lady Miami

Look 2: Dress by Toccin; pumps by Presleys Pumps; ring, bracelets, and earrings — artist’s own

Look 3: Swimsuit and sunglasses by Versace; ring, bracelets, and earrings — artist’s own

Look 4: Suit by Calvin Klein; sunglasses by Tom Ford; necklace by Jennifer Miller; earrings and necklace — artist’s own; Aperol Spritz — courtesy of Jacquelyn Todd

Look 5: Heels by Michael Kors; necklace by Jennifer Miller; dress, belt, ring, bracelets, and earrings — artist’s own