Madelyn Cline's Tommy Hilfiger Look Pays Homage to Fashion's '90s Prep Icons
These exclusive photos prove she belongs in a 'Clueless' reboot.
Madelyn Cline and I are both still wrapping our heads around Tommy Hilfiger’s massive New York Fashion Week Spring 2025 show when we catch up on the phone the morning after. In our defense, there was a lot to take in: 63 avant-nautical looks that mixed madras checks, oversize shirting, and contrasting stripes; a starry guest list including Brooke Shields, Blackpink’s Jisoo, and Cline herself; a surprise finale performance by the Wu-Tang Clan; and perhaps the most headline-worthy setting of the entire NYFW calendar, the decommissioned Staten Island Ferry owned by Saturday Night Live writer Colin Jost and former cast member Pete Davidson.
Cline and I agree: not-quite-setting sail alongside hundreds of other fashion people at sunset was an experience. And, one the ten-year-old versions of ourselves who last rode the ferry with our moms wouldn't believe possible. “I'm seeing the pictures roll through and I'm like, wait, this person was there and that person was there and I know them and I didn't see them! It was…huge,” she laughs.
Madelyn Cline attended Tommy Hilfiger's Spring 2025 show in a look made up of preppy classics, including a white button-up and plaid mini skirt.
Cline says her looked embraced a '90s aesthetic, from her hair to her black loafers.
The Outer Banks star tells me she walked away from the Tommy Hilfiger show feeling inspired by both the remixed layering in the official collection and the all-American outfits all around her in the front row. Cline and every other VIP had similar options to pick from before the event—from prep school checked prints to classic varsity jackets—but the similarities ended once everyone got dressed. “Everybody has their own flavor, the way they style it. They saw something that I saw on the rack and they saw something in it that I didn't, you know? It's like being on a Pinterest Board live.”
Cline got ready with photographer Jocko Graves before arriving downtown for the show.
" I really, really love watching and seeing all of the guests come [to the show] in their outfits," Cline says.
Unbeknownst to Cline, I’d walked by her before the show started and thought she’d peeked at my personal fall 2024 moodboard. She chose the ultimate ’90s prep staples: a white button-up shirt, plaid mini skirt, and black loafers with knee-high sheer black socks underneath. When I asked where the inspiration came from a day later, she name-checked references every New York fashion girl knows well.
“We started mixing and matching and it was giving me Clueless, it was giving me Blair Waldorf, like an early two-thousands, late ’90s vibe,” she says.
Cline says a white button-up is one of her all-time wardrobe heroes.
Cline matched her cherry red nails to the checks on her skirt.
Hair and makeup also got Cline in touch with her favorite throwback references. “It was mostly just clean, natural, easy—let the clothes and the looks speak for itself,” she explains. Translation: an Alicia Silverstone-inspired blowout and a bronzy glow with a little extra eyeshadow “as a nod to the ’90s aesthetic.”
Cline picks out her look before the show.
On her way to the airport, Madelyn Cline tells me we have another thing in common: both our camera rolls are now filled with Tommy Hilfiger reference photos to bring back to our own closets. I’m thinking of a white Oxford freaked to look like it was put on backward over a cream A-line skirt. Cline is fixated on a supersized version of the top she wore to the show, extended to the length of a maxi dress and styled half-open over a pair of baggy jeans.
A Tommy Hilfiger show can't quite be summed up on a phone call, Cline says. "You have to be there, you have to experience it."
“I've been excited to start wearing layers again,” she says. “That's one thing I've been really looking forward to [for fall] and getting ideas for it from this show especially. And the idea for mixing and matching stripes. I've never thought of that before. I'm gonna do that for sure.” Surely she’ll end up on someone else’s Pinterest board when she does.
