Madison Headrick has built a career spanning high-fashion modeling and entrepreneurship, using her platform to support women’s health initiatives along the way. Now expecting her second child, she moves through New York as a familiar presence within its fashion, art, and cultural circles—grounded, visible, on the brink of a deeply personal transformation, and above all else, a true role model for her soon-to-be-born daughter and women of all walks of life. 

V MAGAZINE: Let’s start off with your impressive modeling career. What moments still feel like true “pinch-me” highlights?

MADISON HEADRICK: The first one that comes to my mind is when I was a Prada exclusive. And that was Fall/Winter 2012, and that was like my first real big break. It was my first show. It was my first campaign. It was my first everything. And, you know, coming from a small town in South Carolina, and I was still in high school, and then going from being in a school desk and then the next day being backstage with Pat and Guido and Mica and everyone—I was like, whoa. It was almost like an out-of-body experience. And it was all so new, and I had nothing to compare it to. People can tell you stories, but you don’t know what it’s like until you’re there. I’d never been in a room like that before. 

V: Fashion wasn’t originally part of your world. What was that learning curve like once you were suddenly inside the industry?

MH: It’s funny—I feel like starting so young meant I was learning about fashion and life at the same time. I was scouted at 14, but my parents wouldn’t let me work full-time until I was 18, which is why I graduated early. I was a kid being thrown into a super competitive industry, surrounded by adults who had been doing this for decades. It felt like my first day in the real world. It was the university of life—managing airports, pickups, schedules. When I started in 2012, we didn’t have Uber. I was walking around Italy with a map, trying to figure out how to get to castings. That’s a lot for a kid. But it was amazing. Being in makeup chairs watching the masters work—you absorb everything. It also helped me find my passion for skincare, travel, and beauty. Learning from the best shaped everything that came after.

V: You’ve written about skincare before, but how did Care.ē.on actually go from an idea to a real business?

MH:  I have such a newfound respect for founders now. Everyone told me it was a lot of work, and I thought I understood hard work. Then I started a brand and realized I had no idea what I was getting into. There were so many challenges—manufacturing, shipping, imports, tariffs, and competing with massive beauty companies. I just wanted to start a brand and didn’t realize how much went into it. The reason I started Carry-On was because, as a model, I was sleeping in my own bed less than three months a year. I lived out of a carry-on suitcase because lost luggage couldn’t catch up to me. I needed to master packing and self-care on the go. I was watching everyone on set thinking, “How do you all look so normal?” I was exhausted. Feeling good and looking good go hand in hand, especially when you’re representing a brand. I started creating little kits for myself—something to reset, whether it was a face mist, a mantra, or a cough drop. That’s where Carry-On was born. 

V: You’re balancing modeling, a business, philanthropy, and motherhood. How do you actually manage your time?

MH: It’s super tricky. I used to think I had no time until I had a kid. Now I realize how much I can do in five minutes. I work around my son’s schedule. When he’s awake, I’m fully present—no phone, no computer. When he naps, I go into overdrive: emails, Zooms, meetings, castings. As important as my career and brand are, nothing compares to my son. I’ve learned to choose jobs that align with my values and work with people who understand where I am in my life now. Working mothers are superheroes. It’s incredibly difficult, but it’s so rewarding.

V: Motherhood reshaped your focus on women’s health. How did that experience change you?

MH: I gave birth prematurely, and while everything turned out okay, there was a moment where I was preparing to leave the hospital without my son. The nurses and doctors were incredible. It completely changed how I view healthcare providers and women’s health. That experience pushed me to focus more of my philanthropy on women’s health, research, and science. Every part of my journey—from being scouted to modeling to motherhood—prepared me for this chapter.

This cover story appears in the pages of V159: now available for purchase!

Model Madison Headrick (The Lions)

Photography Luigi & Iango

Fashion Anna Trevelyan

Interview Mathias Rosenzweig

Makeup Georgi Sandev (Forward Artists)

Hair Lauren Berrones (Home Agency)

Producer Alexey Galetskly (AGP NYC)

Studio Manager Francisco Betancourt

Cinematographer Lukas Chmiel

Photo Assistants Tutu Lee

Styling Assistants Damien Loyd & Frankie Benkovic

Production Assistant Justin Barahona

Location Hubble Studios