Who’s That Girl? Quite Possibly the Perfect Match

Before Carolyn Bessette-Kennedy was fashionably thin and shining blond and living in a TriBeCa loft with John Kennedy, she was fuller and darker-haired and a raging party girl.

She prowled the Manhattan clubs until 4 a.m., easily gliding by the velvet ropes that corralled the night livestock. That’s what the beautiful girls did. And it was work, sort of. Sometimes she saw fresh faces she could dress up in Calvin Klein, her employer at the time. She smoked Parliaments. She drank vodka martinis.

Before that, she lived in Boston, where she did marketing for nightclub owners. She got that job after her graduation in 1988 from Boston University; her elementary education degree never led her into a classroom. (How can you face 30 chattering second-graders at 8 a.m. when you’ve been out all night at the Buddha Bar?)

And before that, there was Catholic high school and growing up in affluent Greenwich, Conn., where she lived among a family of strong women. Carolyn, said friends from high school, was not an honor student. She didn’t play sports; she didn’t join clubs. She studied being social.

Her mother, Ann Freeman, has worked as a teacher and administrator in New York public schools. She and Carolyn’s father, William Bessette, divorced when Carolyn was young. A few years later, her mother married Dr. Richard Freeman, who was the chief of orthopedic surgery at a White Plains, N.Y., hospital. He brought three more girls into the family. William Bessette lives in New Rochelle, N.Y., where he works at T N T Kitchen Distributors, a kitchen design firm.

Through all of her life, Carolyn, 30, has been warm, approachable and kind, several people said.

“She is completely, 100% the best listener,” said Paul Wilmot, a Conde Nast vice president who became friends with Bessette-Kennedy when both worked at Calvin Klein. “She is totally empathetic.”

“She tries to make people feel comfortable,” said John Perry Barlow, who met the teenage John Kennedy Jr. when Kennedy spent part of a summer on Barlow’s Wyoming ranch and who attended the couple’s intimate wedding last month on Cumberland Island, Ga. “She understands them emotionally and tries to create comfort in an emotional situation.”

And sometimes she creates the emotional situation. In February she erupted at Kennedy in a New York park and kept yelling in his face, as he pulled a ring off her finger. Then she stormed off screaming, leaving him sitting on the curb, his head buried in his hands. In the workplace, former colleagues said, she was forceful and firm in her opinions, qualities that vary in the telling.

“When I was a freshman and she was a big senior, she was incredibly sweet to me,” recalled Claudia Slocum, a film production coordinator who went to St. Mary’s High School with Carolyn.

“I remember I burst into the girls’ room one day, just sobbing, probably over some lip gloss that my friends had made fun of or something. And she was there with her friends. And she came right over. She dried my eyes and tucked my hair behind my ears and talked me up. And after that, she always smiled and said hi to me in the halls.

“I was always so impressed by that, because I was just a freshman and she was It. She was voted ‘Ultimate Beautiful Person,’ ” Slocum said.

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The instant she said “I do” to John Kennedy three weeks ago, Carolyn Bessette-Kennedy fulfilled that high school destiny and began a new iconography. Freelance photographer Bobby DiMarzo has pocketed a tidy sum selling sultry photos he shot that a Boston magazine ran in 1991.

So stunning was she in the pearl silk wedding dress he designed for her, said Narciso Rodriguez, that “Oh, my God, I thought I was going to pass out. . . . I’ll never see anything more beautiful than that.”

And, as befits such mystique, precious little information has emerged about Herself.

Always, she has had style, the kind that snapped necks, and the willingness to defy convention. In Catholic high school, while all the girls were rolling up their waistbands to shorten their skirts, Carolyn, the really leggy one, was wearing pants.

Later she became a Calvinist. She was working at the designer’s Chestnut Hill, Mass., store when a Klein executive “found her and thought she was fabulous-looking and brought her to New York,” Wilmot said. She donned the uniform of an almost monastic sect of women who adhere to the designer’s high-minimalist style.

It was the early ‘90s. She began her climb through the ranks by selling wholesale to such celebrity clients as actresses Annette Bening and Faye Dunaway. Carolyn wrote millions of dollars’ worth of orders.

“She couldn’t have been more perfectly suited for the role. She looked the part, she knew the clothes, she had wonderful people skills and diplomacy,” Wilmot said. When she left in the spring, after seven years with Calvin Klein, she was the director of show production and earning a salary in the low six figures. Her relationship with Kennedy finally intruded: “How can you talk to the press when you are avoiding the press?” a colleague explained.

Model-tall and a perfect size 6, Carolyn presents herself with calculated casualness. She jams hats on her head, sticks pencils in hair buns. On her honeymoon in Istanbul, she wore a head scarf.

“In the time I’ve known her,” said a woman in the couple’s circle, “she’s been borderline grunge.”

Kennedy, the woman said, “has always made a point of looking like a griz”--just sloppy enough to make people think you aren’t obsessed about your looks--”and she makes a point of looking like an alluring female version of that.”

She carried this shabby chic into her wedding, her bare toes peeking out underneath her incredible slip of a wedding dress, no panty line or seed pearl in sight. She adorned herself with no jewelry and pulled her hair almost carelessly into a ponytail.

“Actually, I wanted to give her pearls, and she didn’t want to wear anything,” said the bride’s intimate friend Rodriguez, who made the gown at the Cerruti atelier in Paris and presented it to her as a gift.

“She’s my muse, so whatever I see her in, I just get this rush. She’s such a beautiful girl, and I don’t mean just physically beautiful, she’s--I sound like a gushing fan, don’t I?--she’s just amazing. I’ll never see anything more beautiful than that.”

And this is her designer talking. Imagine what her husband thinks when he looks at her.

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Carolyn Bessette-Kennedy, said one of her many new in-laws, Kerry Kennedy Cuomo, is “a very bright, sweet, wonderful, creative woman whom John has fallen madly in love with. She has been to the Cape on several occasions, and we all love her. We especially love her because he does.”

And why does he?

A day after their wedding news flew around the world, a publicist sent a Washington Post reporter a book of advice on playing hard to get, along with a hand-scrawled note that read: “Carolyn Bessette followed these rules!” The book advocates that a woman affect mystery and distance to entrap her prize quarry. But friends said Carolyn was not manipulative in her relationship with Kennedy. Rather, she was careful. He carries all that family baggage, see, even after he unloaded a bunch of it at Sotheby’s.

“I think she has fairly good liberated feminist instincts,” said a woman who knows the couple. “She was not one of the women who was saying, ‘How can I make this happen?’ It was more like, ‘Am I sure this is what I want to do?’ ”

The newlyweds were friends for a while before they were lovers and “worked out a lot of the obvious hazards together,” said Kennedy’s friend Barlow. They became engaged a year ago and have lived in his TriBeCa loft since the summer of 1995.

After several months of stealth wedding preparations and a two-week vacation in Turkey and Greece, the new Mrs. Bessette-Kennedy will need some new distractions now that her husband has gone back to work. She could devote herself to her husband’s career--but what, exactly, is his career? Writing thank-you notes for the Tiffany wedding gifts can’t absorb her forever.

“She is quite willing to debate. She’s eager to experience,” said investment banker Liam Dalton, who dated Carolyn in the early ‘90s. “And I’m sure she’s now going to have plenty of things to experience. . . . He’s got somebody who is really a willing participant to live life to its fullest.”

* Special correspondent Dana Thomas contributed to this report.