Madison Bailey Highsnobiety Magazine Issue 33 Frontpage Feature

(Frontpage 181)

Madison Bailey Amplifies Herself

  • Words by Jade Gomez
  • Photographed BySarah Pardini

In this FRONTPAGE interview, actor & model Madison Bailey takes us through her journey towards stardom.

Madison Bailey recalls the early days of her acting career as a bright-eyed 15-year-old, juggling high school by day and call backs by night. It must’ve been cool, right? She jumps in to correct me: “Truthfully, nobody was impressed with what I was doing… I definitely got bullied for being on a stupid show nobody's watching.”

Less than a decade later, everyone is watching Bailey. The multi-hyphenate – actress turned fashion icon – has been thrust into the spotlight as part of young Hollywood’s brightest new class. Now, she’s adding Tommy Girl to the resume. A Tommy Girl is like a brand ambassador, a way for the brand to clasp hands with the people, celebs, and stars making moves in the world Tommy wants to outfit. Since its inception in 1996, with Aaliyah, and the brand’s initial expansion into womenswear, each subsequent chosen “Girl” gets the supercharged boost of the behemoth brand behind their personal brand. Bailey joins a long lineage of Tommy Girls who have helped redefine the brand and its message – and, at the same time, been redefined by the brand. 

When asked what her earliest memory of Tommy Hilfiger was, Bailey immediately calls back to Aaliyah, still the most iconic spokesmodel whose tomboyish style and swag first caught Hilfiger’s eye in the ‘90s. And Zendaya, who announced she was a Tommy Girl in 2018, happens to be one of Bailey’s biggest inspirations.

“I got told that I favored her from a young age. As a younger girl I'm like, Oh my gosh, really? She’s so stunning and so poised and I would say she was my biggest inspiration.”

As the youngest of seven children, Bailey’s parents kept a loose leash on her self-expression. “I feel like my parents really just let me run wild with who I am, with what I want to do,” the 24-year-old actress explains. Small-town living was another story. If you’ve never heard of Kernersville, North Carolina, that’s okay. Bailey doesn’t expect anyone to know it. “Population… 20,000,” she says with a sigh. It’s a quaint middle-class suburb that’s best known as a popular presidential campaign stop, and for its 22-room mansion and tourist attraction, Korner’s Folly. Bailey was always cognizant of the space she took up in Kernersville.

“I felt like I was too big,” she said. “I feel like it was celebrated in my house, and then when I was at school I felt pushed to become smaller or to fit in. You minimize yourself a little bit to click with other people.”

Likewise, growing up in a predominantly white household and town as a mixed-race Black woman was and continues to be a large part of Bailey’s story. “That’s something that I’ve struggled with my whole life,” she says. “Even as an adult, I had confusing moments where I was really just fighting to define myself and maybe putting far too much pressure on myself to fit in either side. I definitely had that desire to connect with my Black half and connect with my culture. I just feel like I lacked guidance in where to connect.”

Madison Bailey Highsnobiety Magazine Issue 33 Frontpage Feature
Madison Bailey Highsnobiety Magazine Issue 33 Frontpage Feature
Top, top worn as skirt, and shoes HILFIGER COLLECTION, Hat TOMMY HILFIGER, Earrings and legwarmers STYLIST’S OWN
Highsnobiety / Sarah Pardini, /

It was moving to the City of Angels that marked a shift in her life. In L.A., Bailey found a place that was big enough to accommodate her personality; it was big enough to let her grow without making her shed the small-town spirit. “If you stay in one place your whole life and you go visit somewhere else, you come back a different person because your world just expands,” she explains. “There's a lot of differences between Kernersville and Los Angeles. It's not only a cultural scope that has grown [in me], but it's also fashion.”

That duality is what connected her to the work of Tommy Hilfiger, whose iconic designs have always been within reach for the working class and the biggest stars. “I think it's cool that it's a brand that works and has weight in both places,” says Bailey. “And that's just the nature of the brand: You really can't define them and you really can't put them in a box.”

Whether over Zoom or onscreen, the actress’ confidence and self-assuredness could fill seven Korner’s Follies. Some people are just destined for the spotlight, and it’s hard to believe the young star was getting bullied at one point for something that comes so naturally to her. The pockets of candid moments, such as those Bailey spent with me bundled up in our respective sweaters in front of our webcams, are her opportunities to shift one’s gaze to meet hers and break the illusion. That’s exactly why she’s in lockstep with the ethos of Tommy Girl, being the larger-than-life representation of the unifying experience of girlhood.

Madison Bailey Highsnobiety Magazine Issue 33 Frontpage Feature
Madison Bailey Highsnobiety Magazine Issue 33 Frontpage Feature
Coat HILFIGER COLLECTION, Sunglasses and earrings STYLIST’S OWN
Highsnobiety / Sarah Pardini , /

These days, Bailey makes the conscious decision to amplify herself. Not by her follower count, celebrity status, or roles, but by what she represents. She has become one of the biggest young stars in Hollywood. After revealing that she’s been out as pansexual on TikTok in 2020 – a time where our phones were our only key to the outside world – Bailey became an integral queer voice in the industry, even if it sometimes rubs up against the complicated relationship she has with the concept of celebrity.

“I'm happy I have a voice where I can speak the positive message in the spaces that I connect with. I feel honored that people could look at me and connect with me without knowing me, but it's a double- edged sword because then there are people who are like, ‘I know everything.’”

As a Tommy Girl representing the ever-changing idea of Americana, Bailey wants to promote confidence above all, from North Carolina to New York. 

“If you're reading this and you're in Kernersville, wear the New York outfit. Wear the outfit because it's great no matter where you're living, I promise.”

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