Everyone Is Obsessed With Carolyn Bessette—But There's Two Other Women We Should Be Talking About.
This Is The Real Plot Twist.
Like it or not—it’s officially the ’90s again.
Kate Moss is back slaying the runway—closing the Gucci F/W show in Milan, no less. Britney is back in the headlines for all the wrong reasons (arrested for drink driving). The Clintons are testifying (but weirdly not Trump). And low-rise jeans, kitten heels, and black turtleneck sweaters—aka the OG of “quiet luxury”—are trending out of control.
Not to mention the entire planet is obsessed with JFK Jr. and Carolyn Bessette Kennedy, thanks to the TV series Love Story: John F. Kennedy Jr. and Carolyn Bessette.
Do you, like me, find waiting a week between episodes literal torture?
As we relive their tragic real-life romance, the media is in overdrive—fueling both new and renewed lust for everything Carolyn Bessette Kennedy. With good reason: The former Calvin Klein publicist turned Queen of Camelot—who famously snagged America’s most eligible bachelor—was the ultimate downtown cool girl.
The Hailey Bieber of her day, if you will.
Bessette was the embodiment of the ’90s minimalist aesthetic—her signature style was chic, understated, and impossibly modern: jeans, trench coats, turtlenecks, and an endless sea of black, black, and more black. Then there’s the platinum gold hair, nearly as famous as she was, which flip-flopped between undone waves, sleek blowouts, low ponies, messy buns, and slicked-back in a headband.
And she could also take the crown as the pioneer of the ‘no-makeup makeup’ look, which women have painstakingly tried to fake for decades.
And lest we forget the influence she had on brides the world over, who, nearly three decades later, are still channeling her 1996 wedding style. If you watched the latest wedding episode, the iconic slip dress was created by then-unknown designer (and her close friend) Narciso Rodriguez—the same man behind Michelle Obama’s unforgettable gown on election night in 2008.
But while all eyes are on Bessette (played by actress Sarah Pidgeon), my attention is firmly fixed on two other women in this story.
First: Daryl Hannah—the ’90s actress who shot to fame as the sexy mermaid in Splash and who dated JFK Jr. from 1988 to 1994. Hannah herself is trending again after penning a scathing essay for The New York Times over her portrayal in the series as the shallow, irritating, unstable ex-girlfriend.
The headline? How Can ‘Love Story’ Get Away With This?
Ouch.
And last—but even more importantly—Caroline Kennedy: the stoic, fiercely private sister of JFK Jr. and the sole surviving child of President John F. Kennedy and the legendary Jackie Kennedy Onassis (played to perfection by Naomi Watts).
But I’m not actually referring to the real-life Caroline Kennedy here.
I’m talking about the actress portraying her in the series—the formidable Grace Gummer.
If Bessette has been cast as the pin-up of ‘quiet luxury’, Kennedy—or rather Gummer—is without doubt the queen of ‘elegant luxury’.
And here’s where things get personal.
I was lucky enough to have tea with the then-buzzy up-and-coming Gummer—now 39—eight years ago in a café in her then-neighborhood of Dumbo, Brooklyn.
You can read the full interview here.
Gummer—who you may or may not realize is the daughter of the iconic Meryl Streep—was an indie theatre darling who landed her big break in Arcadia on Broadway in 2011. TV roles in The Newsroom and American Horror Story followed, earning her a reputation for playing smart, complex women with real depth.
This is undoubtedly why she was chosen to step into the poised, old-worldly shoes of American royalty, Caroline Kennedy.
A role of a lifetime that she has made her own.
What you also may not know is that Gummer studied art history and Italian at Vassar and contemplated becoming a costume designer before a theater director friend sent her a script that changed everything.
Meeting Gummer all those years ago, it was clear she was well on her way.
Watching her now transform into Caroline Kennedy—with her composed demeanor, political savvy, and regal-like restraint—has been fascinating.
Here are a few highlights from our interview, Gummer’s thoughts on style, and how she approached becoming the classy, enigmatic Caroline Kennedy.
Grace Gummer “Modeled” For A Max Mara Shoot For Harper’s Bazaar
“I really understand why supermodels are paid a gazillion dollars. It’s 95 degrees, I’m wearing wool pants and cashmere sweaters, cars are coming in every direction, and the photographer is yelling, ‘Smile! Okay—back, front, turn around, hop in the air!”
The Actresses Who Inspire Her
Carey Mulligan, Sarah Paulson, and Claire Danes. “They’re my friends—but I also genuinely admire their work.” Just don’t mention Meryl.
Fame Quietly Elevated Her Fashion Game
Gummer was a fixture in the front row at Michael Kors, Proenza Schouler, Calvin Klein, Tory Burch, and Khaite during New York Fashion Week. “Khaite makes up about 40 percent of my wardrobe. I don’t go to work in sweatpants anymore, I’m a little bolder now.”
One Vintage Shirt Helped Her Find Caroline Kennedy
An' 80s-vintage Valentino striped shirt helped unlock the character. “The moment I put it on, I thought—oh, here she is. It has a little bit of a shoulder, buttons all the way to the top, and the most beautiful fit. It’s one of those pieces that just couldn’t be replicated today.”
Gummer Deeply Respects Caroline Kennedy
“I think she has impeccable style—and still does. I have so much admiration and respect for Caroline. She’s such a strong, powerful woman of integrity. Fundamentally decent, intensely private—and in our show, she becomes an incredibly important voice of reason for John.”
5 Things You May Not Know About The Real Caroline Kennedy
1. She Has Lived Through Unimaginable Grief
Kennedy was just six when her father was assassinated in 1963, lost her mother, Jackie Kennedy Onassis, in 1994, and then her brother John Jr. in the 1999 plane crash that also claimed Carolyn Bessette Kennedy and her sister Lauren. And heartbreakingly, her daughter Tatiana Schlossberg passed away in December 2025 at 35 from acute myeloid leukemia.
2. She’s A Respected Diplomat
The Kennedy matriarch served as U.S. Ambassador to Japan from 2013–2017 and is currently serving as U.S. Ambassador to my homeland of Australia.
3. She’s A Political Author
Kennedy has published several books on American history, poetry, and constitutional rights, including In Our Defense: The Bill of Rights in Action.
4. Her Son Is Following His Grandfather Into Politics
Jack Schlossberg—JFK Jr.’s nephew—has emerged as a vocal political voice and has become increasingly active in Democratic politics.
5. She Remains An Enigma
Despite being born into America’s most scrutinized political dynasty, Kennedy has spent her life fiercely guarding her privacy—making her portrayal in the series all the more fascinating.
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