Haley Bennett Believes In Always Breaking Fashion Rules


Actress Haley Bennett is no stranger to playing complex women. She's portrayed a pregnant housewife compelled to consume dangerous objects (Swallow), a vengeful widow (The Magnificent Seven), and a married woman at the center of a missing person's case (The Girl on the Train), but perhaps none had higher stakes than CIA agent Sidney Scofield in the new Apple TV+ series The Last Frontier. The heart-pounding drama from Jon Bokenkamp, the creator of The Blacklist, kicks off in thrilling fashion when a prison transport plane crashes in the remote Alaskan wilderness, setting free dozens of dangerous inmates and upending the quiet, snowy town of Fairbanks. From there, a windy espionage mystery unfolds as U.S. Marshal Frank Remnick (Jason Clarke) and CIA operative Scofield work together to corral the violent criminals. Viewer beware: Nothing is as it seems.
For the show's NYC premiere earlier this week, Bennett eschewed classic prettiness for powerful simplicity. Opting for an all-black Fforme look consisting of a sleek tank and maxi skirt cinched with a horsehair belt with her hair pulled back into a sleek bun to reveal sculptural diamond earrings, Bennett was a breath of fresh air. She's not one to follow fashion rules, and stripping away any noise for quiet luxury felt like an act of rebellion.
Surrounded by a library of books and her closest friends, Bennett embraced showing up as her truest self for the evening. The next day, we caught up with the actress to talk about all of the chic details, including how she and her makeup artist Alice Lane achieved her perfectly glowy, sun-kissed makeup. Keep reading for our exclusive interview.
What excited you about The Last Frontier and the role of Sidney Scofield?
The Last Frontier scripts were incredibly high-stakes and complex. [It was] a challenge to keep it grounded. You have to fully commit. There are a lot of cliff-hangers. Sidney is fighting her demons, literally and figuratively. She can come across shrewd and arrogant. She is very flawed, cunning, and strategic—always thinking ahead. [The] CIA agent [is] full of contradictions, secrets, each one carrying immense weight throughout the season. Sidney is forced to make impossible choices while fighting to protect something deeply important to her, even when those choices have catastrophic consequences. Beneath all the chaos and action, she's on her own mission, an avenging angel wrestling with guilt, shame, redemption, and the pursuit of truth at any cost.
What should audiences be prepared for when watching the series?
Nothing is what it seems. There's action, mystery, and a surprising amount of emotion and heart. The cast really did a great job making this stuff believable and relatable. The relationships evolve with every episode, becoming more complex, unexpected, and human.
You just celebrated the show's premiere in NYC. Tell us about the look and what inspired it.
Simplicity. Feminine but strong. For years, I hid behind clothes, behind characters, armor, fantasy. I'm in a phase of wanting to strip that away, how I can show up as my truest self and challenge the norm and live in my power. Not prettiness. Being yourself in this world feels like rebellion. I like that. The horsehair belt was a quiet nod to The Last Frontier, a tether back to the world we built.
Do you have any guiding philosophies for red carpet dressing?
Break the rules—always.
Take us inside your getting-ready rituals. What's the vibe?
Started with a glass facial and full-body microdermabrasion. That was a special treat. I felt like a baby seal. We prepared in a library, surrounded by books, calm, music, and imagination. My cousin Taylor and my friend Taylor were with me. Their support meant everything. After nearly two years away filming, this premiere felt like a pause, a breath before going home. I don't know what the future holds, but that uncertainty feels thrilling.
Your earrings were a standout. What's the story behind them?
They were chosen by Rose Forde. She always finds pieces with a twist, like the black feather headpiece I wore for Widow Clicquot at the Toronto International Film Festival. These earrings had that same spirit—unexpected, sculptural, and a little defiant, like Sidney herself.
What was your vision for hair and makeup?
Simple and honest. I often do my own makeup on set. It used to be the norm for performers, and no one knows my face better than I do. Ironically, I travel with cases of makeup and end up wearing almost none. There's an art to looking like you're not wearing any. Alice Lane, who I've worked with for years, is a true artist. She paints my face with nuance, never heavy, never flat. Our faces aren't one color, and I never want to look like I'm wearing a mask. Less is always more for me. I have delicate features, and I'm drawn to authenticity over pageantry. There's a time for drama, and there's a time to simply be oneself and uncover.
You had a gorgeous sun-kissed look—what products did Lane use?
We used an old-fashioned matte artistry palette The textures are almost waxy (nothing like commercial makeup) but applied with the lightest touch. Alice approaches makeup like painting, layering tones rather than covering. It's a patchwork of color, never a mask. She even melts down lipsticks to create her own shades. Our process is intuitive and collaborative. We also played with Ilia products. Their colors and textures are beautiful, and Vintner's Daughter was the star of the show. It gave my skin an insane, natural glow and smells divine. I didn't wear any base at all. I want my skin to feel alive.
How did you feel stepping out in your final look?
The snowy carpet transported me right back to Alaska and the world of The Last Frontier. Energetically, I felt high, vibrant, alive. These past few years have taught me so much. After inhabiting so many characters, it felt rare and beautiful to simply be myself. I'm filled with gratitude for the work that has both sustained and awakened me. Now, I'm excited to release it into the world, to let it become whatever it's meant to be.
The Last Frontier premieres on October 10 on Apple TV+.
Photographer: Patrick Donovan
Hairstylist: DJ Quintero
Makeup Artist: Alice Lane
Manicurist: Tara Haye

Jessica Baker is Who What Wear’s Executive Director, Entertainment, where she ideates, books, writes, and edits celebrity and entertainment features.