Charles Gandee’s “Goodbye to All That” first appeared in the September 1999 issue of Vogue.

He was no prince, and she was no Cinderella. Despite the media’s constant portrayal of them as a “fairy tale” couple—as America’s “royalty”—they were the exact opposite. She chose headbands over tiaras; he rode a bicycle, not a white horse. Their home was a loft, not a castle, and outside sat a black Saab instead of a golden carriage. This very reality made 33-year-old Carolyn Bessette Kennedy and 38-year-old John F. Kennedy, Jr. more fascinating than any storybook pair with a “charmed life.” By blending modernity with the classic allure of youth, beauty, wealth, power, fame, breeding, poise, and style, they possessed a unique magic: the ability to captivate the public imagination and remain, for better or worse, the constant center of attention.

For him, the flashbulbs began flashing on December 9, 1960, as he left Georgetown University Hospital with his mother—just fourteen days after his premature birth and 31 days after his father was elected President. For her, it started on the evening of September 21, 1996, as she emerged from a church on Cumberland Island in a sleek, bias-cut silk dress, her radiant smile meant for a few dozen guests but seen by millions around the world.

Though accustomed to privilege and wealthy suitors, only someone mentored by Jacqueline Onassis could have been prepared for the intense spotlight focused on the woman who won the heart of the little boy who saluted his father’s coffin in 1963. The tabloids instantly crowned her “Camelot’s New Queen,” and even Newsweek declared her a fashion icon for the 90s. Months later, the British press cruelly suggested the honeymoon was over, claiming she was trapped and crying in her “tower.” If she was distressed, she never spoke of it to the press—a lesson perhaps learned from the mother-in-law she never met.

In the countless published photos from that time, she often appeared like a startled, confused rabbit—an expression unfamiliar to those who knew her. In reality, it was her confident ease and spirited charm that had propelled her from a job at a Boston mall to handling celebrity clients for Calvin Klein in New York, eventually becoming the PR director for his flagship division. Then she met Kennedy, and increasingly had to slip out of her office through the service entrance.

Before becoming Mrs. John F. Kennedy, Jr., she might have blended in with the many young brunettes who had gone blonde around the city.She used to leave her Birkin bags fashionably open, but at a certain point she clearly decided to break from that image. The first sign of her independent streak came when she asked her friend Narciso Rodriguez—whom she met when he was an unknown designer in Calvin Klein’s studio—to design her wedding dress. Later, realizing that the girl voted “the ultimate beautiful person” by her Greenwich, Connecticut, high school classmates might benefit from a bit of edge, she began appearing at charity balls and black-tie dinners in Versace or, increasingly, Yohji Yamamoto. Two images stand out: her shaking hands with British Prime Minister Tony Blair last year in black opera-length gloves and a black strapless Yamamoto gown, and her at the White House Correspondents’ Dinner this year, nuzzling against her husband in a double-breasted evening suit with peaked lapels and a Bakelite fan necklace from Jean Paul Gaultier’s spring ’99 couture collection.

When the press noticed his wife’s emerging style, her husband glowed. “You gotta see the back; the back’s the best part,” he once told a reporter asking about a particular dress. But Kennedy had long navigated the minefield of public life, honing his skill at disarming reporters with a winning mix of candor, wit, and charm—especially handy when headlines like “The Hunk Flunks” and “The Sexiest Man Alive” hit newsstands. He also showed dignity and grace that countered his sometimes precarious image. Standing outside 1040 Fifth Avenue on May 20, 1994, he broke the news the world dreaded, facing the crowds with remarkable poise: “Last night, at around 10:15, my mother passed on.…”

Yet he also had a provocateur’s streak, a tendency to bait the press. In 1995, launching George, he invited Madonna—with whom he was “linked,” as the papers put it—to write a piece titled “If I Were President.” A year later, he persuaded Drew Barrymore to dress as Marilyn Monroe, recreating Monroe’s 1962 performance of “Happy Birthday, Mr. President” at Madison Square Garden.

Like his mother, who used her influence to save Grand Central Terminal from demolition or protect Central Park from a planned skyscraper, he understood the power of celebrity—including his own—and how to harness it for causes he cared about, whether selling magazines or drawing attention to worthy efforts. Six years ago, he agreed to sit for a portrait by Annie Leibovitz and an interview with then-editor-at-large William Norwich, on one condition: the article had to focus on the John F. Kennedy Profile in Courage Award, established in 1989 to honor “exemplary acts of political courage by elected officials,” and the portrait had to include lawyer and civil rights activist Elaine R. Jones, then a member of the award’s voting committee. When Norwich couldn’t resist asking if he ever considered running for office, Kennedy didn’t bolt. Instead, he paused and said, “I have to admit it is something I consider a lot.”

Would he have done it? Or would he have stayed with George, the fragile magazine he was determined to make a success? And would his wife have embraced the opportunities her marriage presented with the same savvy she showed in her first role as Mrs. John F. Kennedy, Jr.? If so, which opportunities?

No one likes unanswered questions—especially these.

Frequently Asked Questions
FAQs The Enduring Allure of John F Kennedy Jr Carolyn BessetteKennedy

BeginnerLevel Questions

Q Who were John F Kennedy Jr and Carolyn BessetteKennedy
A John F Kennedy Jr was the son of President John F Kennedy and Jacqueline Kennedy Onassis Carolyn BessetteKennedy was a fashion publicist who became his wife They are remembered as a glamorous iconic couple of the 1990s

Q Why are they still so famous today
A Their story combines American royalty timeless style tragic mystery and a what could have been narrative They represent a peak of 90s glamour and their untimely deaths in a 1999 plane crash cemented their status as a legendary frozenintime couple

Q What was so special about their style
A Carolyn in particular was a minimalist fashion icon Her simple slip dresses tailored pantsuits and understated elegance defined 90s cool and remain influential John Jr embodied a classic athletic American look

Q How did they die
A On July 16 1999 John piloted a small plane headed to Marthas Vineyard With Carolyn and her sister Lauren aboard the plane crashed into the Atlantic Ocean The cause was attributed to pilot error due to spatial disorientation in hazy conditions over water at night

Advanced Detailed Questions

Q Beyond the glamour what was their relationship really like
A While publicly perfect accounts suggest a complex intense marriage They were fiercely private but faced immense media scrutiny Reports indicate normal marital ups and downs magnified by the unbearable pressure of constant public attention

Q What is the enduring allure or fascination really about
A Its a layered phenomenon Nostalgia for a presocial media analog era of celebrity Mythmaking around American royalty the Tragic Arc of a family marked by repeated public tragedy and the Aesthetic Legacy of Carolyns specific influential style

Q Were there any controversies or lessdiscussed problems in their story
A Yes The intense paparazzi harassment they endured is a major oftencritic