Enter Smiling, the Stylish Carolyn Bessette

Enter Smiling, the Stylish Carolyn Bessette

By ELISABETH BUMILLER

Published: September 29, 1996

Since her marriage last weekend to John F. Kennedy Jr., Carolyn Bessette has been breathlessly described as the beautiful and brainy new Queen of Camelot. Interviews with friends and former colleagues reveal a more recognizable young woman: a child of affluent suburbia, with less interest in academics than in downtown clubs, whose extraordinary looks, sophistication and ambition propelled her rapidly upward through the fashion industry in New York.

Armchair Freudians have also noted the many similarities between Ms. Bessette-Kennedy, as she has chosen to be called, and Mr. Kennedy's famous mother, the late Jacqueline Kennedy Onassis.

Like Mrs. Onassis, Ms. Bessette-Kennedy is Roman Catholic and the product of divorced parents, with a French name if not heritage. Like Mrs. Onassis, Ms. Bessette-Kennedy is athletic, with an almost mysterious allure in public and, former colleagues say, a short temper in private. And like the image-conscious Mrs. Onassis, who directed her designer, Oleg Cassini, to create the look of pillbox hats and boxy suits that became her trademark as First Lady, Ms. Bessette-Kennedy, 30, worked closely for months with her designer and had two de rigueur couture fittings in Paris of three hours each to create the wedding dress estimated at $40,000 that she wore in the tumbledown church on Cumberland Island off the coast of Georgia last weekend.

''It's a very sensuous dress,'' said her friend and designer, Narciso Rodriguez of the Design House of Nino Cerutti, who made his pearl-colored silk crepe creation a gift to the bride. ''That's what we both wanted from the beginning.''

The Kennedys, spotted last week honeymooning in Istanbul (where she was photographed in a Jackie-ish head scarf and sunglasses), have not announced a date for their return to New York. But their marriage -- a nexis of youngish fashion, media, politics and celebrity -- has already set off speculation about which Manhattan social circles, if any, they will choose for themselves. Mr. Kennedy, 35, the editor of the political monthly George, grew up on Fifth Avenue but in his adult life has largely ignored his mother's Upper East Side milieu.

''Frankly, I don't blame him,'' said Pat Buckley, a denizen of that world. Ms. Bessette-Kennedy, a former public relations executive at Calvin Klein, who made her mark at the design house in her early 20's by selling privately and well to Mr. Klein's celebrity friends, has spent long hours in Manhattan nightclubs.

Will the two keep their lives largely quiet and downtown, and continue to live in Mr. Kennedy's TriBeCa loft? Will Ms. Bessette-Kennedy have a promotional hand in George, a magazine thick with ads but thin, critics say, in content? Will they have children, and will Ms. Bessette-Kennedy go back to a job? Will the president's son ever run for public office? Whatever they do, friends say, their lives will be under more scrutiny than ever. George Plimpton, a longtime friend of the Kennedy family, remembers how Mr. Kennedy's arrival at a recent benefit for Mr. Plimpton's Paris Review stopped guests in their tracks. ''It was embarrassing,'' he said. ''I was just so sorry. I think it's going to be very difficult for them to fit in.''

One thing is certain: The spotlight in New York has moved for now from Mr. Kennedy to Ms. Bessette-Kennedy, much as it did for Diana Spencer 15 years ago when she married the Prince of Wales. Fittingly, the now-divorced Diana has taken note of what passes in America for royal marriage. ''She said she wished she had been able to get married in such a private way,'' Anna Wintour, the editor in chief of Vogue, reported of a conversation she and Diana had in Washington last week. ''But she said her family would never allow it.''

Fashion editors, meanwhile, are eager to anoint Ms. Bessette-Kennedy as a new icon of fashion.

''We'd love to have her on the cover,'' said Liz Tilberis, the editor in chief of Harper's Bazaar and a Calvin Klein devotee. ''She's going to be an amazing symbol of American style.''

An Early Member Of the 'In' Crowd

Carolyn Bessette grew up in a large house on Lake Avenue in Greenwich, Conn., by all accounts a stable background for a young woman whose friends describe her as warm and exuberant. Her mother, Ann Freeman, worked as a teacher and an administrator in the Chappaqua public school system, and her stepfather, Dr. Richard Freeman, was the chief of orthopedic surgery at White Plains Hospital. Her father, William Bessette, is an architectural engineer in White Plains.

She attended St. Mary's High School in Greenwich, although a friend from Calvin Klein recalls that Ms. Bessette-Kennedy once told her that she had started at Greenwich High School ''but that her parents pulled her out because she was having too much fun.''

St. Mary's, which is defunct, was not as academically rigorous as Greenwich High, and the teen-age Carolyn Bessette seems to have had fun there, too.

''She was in the beautiful 'in' crowd,'' recalls Meg Nash, who was a year behind Ms. Bessette-Kennedy in school. ''She went to all the right parties.''

Ms. Bessette-Kennedy graduated in 1983 and went on to Boston University's School of Education. In Boston, she also briefly pursued a modeling career and hired a photographer to take pictures of her for a professional portfolio.

She dated a campus hockey star, John Cullen, who now plays for the Tampa Bay Lightning, and appeared on the cover of a calendar called ''The Girls of B.U.'' After four and a half years of college, she graduated in January 1988 with a degree in elementary education, and soon had a job as a saleswoman at the Calvin Klein boutique in Boston's Chestnut Hill Mall.

In no time, her beauty and style were brought to the attention of a Calvin Klein executive in New York, Susan Sokol, who was looking for a woman to handle Mr. Klein's celebrity clients.

Carolyn Bessette was recommended to Ms. Sokol by a traveling sales coordinator who had visited the Boston store.

''Carolyn fit the bill perfectly,'' said Ms. Sokol, who was then a president at Calvin Klein.

''She was absolutely charming, she was completely refreshing, she was completely outgoing.'' Here was a young woman, Ms. Sokol said, ''who wouldn't feel intimidated working with these kinds of people.''

Ms. Sokol's instincts were right. A former colleague at Calvin Klein said Ms. Bessette-Kennedy quickly established herself as savvy beyond her years, the perfect saleswoman for important clients like the television correspondent Diane Sawyer, the socialite Blaine Trump and the actress Annette Bening, who all ordered privately from Mr. Klein's showroom.

''She would guide them through the collection, tell them what looked good on them, and advise them on how to put it all together,'' said Paul Wilmot, who was then Calvin Klein's vice president for public relations. ''It was a wonderful thing. She sold millions of dollars of clothes over a period of time.''

Ms. Bessette-Kennedy was herself the best advertisement for Mr. Klein's clothes, and her all-American beauty the perfect public face for a design house, where image is crucial. Former associates say she was one of the designer's muses, close to both Mr. Klein and Kelly Klein, now separated from her husband.

''She was 'The Look,' '' said a former Calvin Klein employee, who remembers how Zach Carr, a designer for Mr. Klein, would often say, ''I wonder how Carolyn would put this together.' ''

Former associates still talk about Ms. Bessette-Kennedy's sense of style. One remembers the day she turned up at the office wearing a tight black leather Calvin Klein jacket as a blouse, set off by the thick blond mane she often wore fashionably unkempt in the ''bedroom hair'' style much in vogue on the runways.

Frequenting Clubs For Work and Play

In her seven years at Calvin Klein, Ms. Bessette-Kennedy moved up from celebrity sales to a director of public relations to director of show production, a job that gave her responsibility, among other things, for Mr. Klein's fall and spring shows in Bryant Park. While many in the industry assumed her job was more image-building than anything else, that of a woman who turned up for work when she wanted, insiders say she kept long hours and was demanding, opinionated and vocal.

''She is sharp as a razor,'' said one friend in the industry. Ms. Bessette-Kennedy was said to be especially good at casting models for shows, and often scouted for new faces in the nightclubs where she had gone for years.

''She was one of our favorites because she was such a cool girl,'' said David Rabin, an owner of Rex, a club that was popular for 18 months in the early 1990's. ''She was a part of the Rex family.''

Mr. Rabin said that Ms. Bessette-Kennedy went to Rex about three times a week, and that Mr. Kennedy occasionally turned up, too. It is unclear if the two noticed each other there, just as it is unclear where they officially met, since friends scoff at reports that the two first encountered each other jogging in Central Park.

Whatever the case, they began dating about two years ago, were engaged last September, and in February had a public shoving match in Washington Square Park that was caught on video.

Ms. Bessette-Kennedy quit her job at Calvin Klein in the spring. Good friends speculate that she was tired of the work after seven years, was not happy with changes in the Calvin Klein management, and wanted time to plan her wedding. Not such good friends speculate that Mr. Klein did not like it when Ms. Bessette-Kennedy, at times, got more publicity than his clothes.

In any case, she subsequently asked her friend Mr. Rodriguez over a drink at the restaurant Odeon to design her dress, which set Mr. Rodriguez off on a three-month marathon. He made, he said, three final versions of the dress, in various luxurious fabrics, but would not discuss cost.

''I'm one of those bad designers who buys really expensive fabrics and then cuts into them,'' Mr. Rodriguez said. ''And then later Mr. Cerutti comes to me and says, 'Hey, are you trying to break me?' ''

Carolyn Bessette and John Kennedy Jr. were married before 40 family members and friends on Saturday, Sept. 21, in a 19th-century church decorated with native wildflowers and vines on Cumberland Island, a national park that is 18 1/2 miles long and 4 miles wide. A reception was held at the island's Greyfield Inn. The wedding was kept a secret, so no helicopters with photographers buzzed overhead.

An announcement was released afterward by the bridegroom's uncle, Senator Edward M. Kennedy, and included a description of the couple's three-tier wedding cake with vanilla butter-cream frosting decorated with flowers.

The couple, the announcement concluded, will live in New York City.