NEW YORK, NY.- The term icon is often overused, but in the case of Carolyn Bessette- Kennedy, her iconic status is undeniable. An irreplaceable figure, captivating the world with her timeless elegance, minimalist style, and what is known today as “quiet luxury,” Bessette-Kennedy remains one of the most recognized and revered fashion icons of the 20th century. A publicist for Calvin Klein, she was at the epicenter of American fashion in the 1990s, and following her marriage in 1996 to John F. Kennedy Jr., she was thrust further into the public eye. Her dedication to fashion, coupled with her indomitable spirit, continues to inspire many, even 25 years after her tragic passing.

This December, Sotheby’s will present three historically significant garments from Carolyn Bessette-Kennedy’s personal collection in the second annual “Fashion Icons” auction in New York. These remarkable pieces, appearing on the market for the first time, were gifted by the style icon to her close friend, RoseMarie Terenzio, who was John F. Kennedy Jr.’s executive assistant, publicist, and one of the couple’s closest confidantes during the 1990s.

The auction will open for online bidding on 27 November and close 17 December with the garments displayed at Sotheby’s New York 5 – 10 December. “There is no greater expression of someone’s life than their clothes. Countless articles have been written about Carolyn’s life and era-defining minimalist style, yet relatively little exists on public record of her own voice. These garments speak volumes about her tragically short but remarkable life. They reveal a woman who made considered choices, navigated public scrutiny with intelligence and grace, displaying a generosity and kindness that touched those around her. Carolyn Bessette-Kennedy understood the power of dressing well, and this belief is forever reflected in these clothes” --LUCY BISHOP, SOTHEBY’S FASHION SPECIALIST

These items, personally consigned by Terenzio, reflect the deep friendship and shared history between her and Bessette-Kennedy; each piece telling a story of a woman who navigated the public eye with grace, intelligence, and an unwavering sense of style.

Terenzio recalls the significance of these garments in her New York Times bestselling memoir, Fairy Tale Interrupted: A Memoir of Life, Love and Loss (2012), describing the style icon as her “fashion fairy godmother.” She remembers when Bessette urged her, then 27, to try on the vintage faux leopard doublebreasted coat to wear on a first date. “She said, ‘It looks perfect on you. You should keep it. I’ve been photographed in it so many times, [the media] are going to start making fun of me.” The statement piece, which carries an estimate between $20/30,000, is a favorite of Terenzio’s, who now works as a strategic communications and crisis management.

“Carolyn has left an indelible mark on fashion and on those who knew her. Her pieces are symbols of a woman that continues to inspire style and captivate the public’s imagination. These historical pieces deserve to be cherished and properly preserved, to honor Carolyn’s legacy and ensure she is remembered.” --ROSEMARIE TERENZIO

Terenzio has intentionally selected Sotheby’s to host the collection, recognizing the auction house’s longstanding commitment to preserving the Kennedy legacy. This relationship dates back to 1996, when JFK Jr. personally chose Sotheby’s to handle the estate sale of Jacqueline Kennedy Onassis.

INSIDE THE COLLECTION

“What strikes me most about Carolyn’s wardrobe is its practicality – these are the clothes of a woman rushing through the bustling streets of New York and attending exclusive evening affairs. Her choices were practical, but she always looked polished – she understood the power that fashion can hold in the everyday life of a woman. That’s the secret behind why her style remains so widely admired and emulated by women around the world today. These garments reflect the remarkably normal life of an extraordinary woman, whose personal taste continues to influencemodern fashion and define American style.” --LUCY BISHOP SOTHEBY’S FASHION SPECIALIST

Vintage Double-Breasted Faux-Leopard Fur Coat
Circa 1969
Unlabeled, with PU leather piping, broad lapels, chunky metal buttons and two slit pockets Bust 92 cm (36 in), shoulder 41 cm (16 in), 102 cm (40 in) length Estimate: $20,000 - $30,000

In 1996, RoseMarie Terenzio was preparing for a first date with a “good-looking media pundit” and discussed her outfit dilemma over the phonewith Carolyn Bessette- Kennedy. Summoned to the couple’s TriBeCa loft, 27-year-old RoseMarie recalls in Fairy Tale Interrupted: A Memoir of Life, Love and Loss: “Whenever I had a date, Carolyn would say, ‘What are you wearing? Come down, and we’ll pick something out for you.’” RoseMarie fondly describes Carolyn as her “fashion fairy godmother.” That day, Bessette-Kennedy pulled an eye-catching vintage faux-leopard coat from her closet and urged Terenzio to try it on, exclaiming, “It looks perfect on you. You should keep it. I’ve been photographed in it so many times [the media] will start making fun of me.” While the date didn’t last, the coat did, becoming a treasured piece in RoseMarie’s wardrobe for the next 25 years.

Reflecting on that era, Terenzio fondly remembers becoming the envy of George magazine staffers after Bessette took her under her wing: “People in the office were jealous. They’d say, ‘Oh, she’s trying to look like Carolyn.’ And who wouldn’t want to look like her?”

Carolyn Bessette-Kennedy was photographed in the coat alongside her husband John F. Kennedy Jr. in 1995 or 1996. RoseMarie herself was photographed wearing the coat, walking with John F. Kennedy Jr. in 1996.

Interestingly, this original coat dating from circa 1969, comprises many of the design features seen on the runway for Prada’s Autumn-Winter 1996-97 collection, which heavily drew inspiration from that particular period in fashion.

Prada Single-Breasted Black Double-Faced Wool Coat 1997
Labeled, size IT 40, with two patch pockets and belt with large plastic buckle. Bust 92 cm (36 in) max, shoulders 39 cm (15.5 in), length 106 cm (42 in) Estimate: $15,000 - $20,000

Carolyn Bessette-Kennedy was photographed wearing this coat, accessorized with her signature narrow oval sunglasses, a Prada Spazzolato bag, and a vanity case, while clutching a roll of gift wrap as she exited the couple’s TriBeCa apartment en route to Bill Clinton’s inauguration on January 19, 1997. On another occasion, she wore the coat paired with jeans while walking the couple’s beloved dog, Friday. A favorite in her wardrobe, Carolyn was photographed in several variations of this Prada coat, including beige and red tweed. Likely from Prada’s Autumn-Winter 1996-97 collection, the coat reflects the slim silhouette and retro influences of late 1960s and early 1970s designs.

Yohji Yamamoto Black Wool Double-Breasted Jacket, 1997
Labeled, size XS Bust 86 cm (34 in), waist 66 cm (26 in) Estimate: $15,000 - $20,000

Historically inspired with padded hips, a tightly fitted waist, and self-covered buttons, this piece is paired with an associated Junya Watanabe for Comme des Garçons black polyester skirt, known for its unique construction designed to be worn ‘back-to-front.’ From the Autumn- Winter 1998-99 collection, the skirt is labeled, with a waist measurement of 78 cm (31 in).

Carolyn Bessette-Kennedy was photographed wearing this jacket while attending the prestigious Jacqueline Kennedy Onassis Medal event in New York City on March 4, 1997. The event, held in honor of Robert DeNiro, celebrated his contributions to the arts and the city’s cultural landscape. Accompanied by her husband, John F. Kennedy Jr., the couple’s appearance drew significant media attention, symbolizing their status as American icons of style and sophistication.